Use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides or their salts for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor herbicides

ABSTRACT

Use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides of formula (I) or salts thereof 
                         
with R, X, A, and Z having the meaning as defined in the description,
 
for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor herbicides by containing one or more chimeric gene(s) comprising (I) a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a)  Avena , (b)  Pseudomonas , (c) Synechococcoideae, (d) Blepharismidae, (e)  Pseudomonas , (f) Picrophilaceae, (g) Kordia, or (II) one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably from  Pseudomonas , or (III) one or more DNA sequences encoding mutated maize ( Zea mays ) or soybean ( Glycine max ) HPPD each being mutated as described in WO 2012/021785.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a § 371 National State Application of PCT/ EP2015/054972, filed Mar. 10, 2015, which claims priority to European Application No. 14158715.4 filed Mar. 11, 2014.

BACKGROUND OF THE INVENTION

Field of the Invention

The invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides or their salts for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor herbicides.

Description of Related Art

WO2012/126932 discloses several new N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides and their use as HPPD inhibitor herbicides for weed control.

However, the herbicidal activity of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides might cause damages on several crop plants which limit their use in such crop growing areas as herbicides for weed control.

HPPD inhibitor herbicides can be used against grass and/or broad leaf weeds in crop plants that display metabolic tolerance, such as maize (Zea mays) in which they are rapidly degraded (Schulz et al., (1993). FEBS letters, 318, 162-166; Mitchell et al., (2001) Pest Management Science, Vol 57, 120-128; Garcia et al., (2000) Biochem., 39, 7501-7507; Pallett et al., (2001) Pest Management Science, Vol 57, 133-142). In order to extend the scope of these HPPD inhibitor herbicides, several efforts have been developed in order to confer to plants, particularly plants without or with an underperforming metabolic tolerance, a tolerance level acceptable under agronomic field conditions.

Meanwhile transgenic plants have been engineered by by-passing HPPD-mediated production of homogentisate (U.S. Pat. No. 6,812,010), overexpressing the sensitive enzyme so as to produce quantities of the target enzyme in the plant which are sufficient in relation to the herbicide has been performed (WO96/38567).

Alternatively, transgenic plants have been generated expressing HPPD proteins that have been mutated at various positions in order to obtain a target enzyme which, while retaining its properties of catalysing the transformation of HPP into homogentisate, is less sensitive to HPPD inhibitor herbicides than is the native HPPD before mutation (for example see at EP496630, WO 99/24585).

More recently, the introduction of a Pseudomonas HPPD gene into the plastid genome of tobacco and soybean has shown to be more effective than nuclear transformation, conferring even tolerance to post-emergence application of at least one HPPD inhibitor (Dufourmantel et al., 2007, Plant Biotechnol J. 5(1):118-33).

In WO 2009/144079, a nucleic acid sequence encoding a mutated hydroxyphenylpyruvate dioxygenase (HPPD) at position 336 of the Pseudomonas fluorescens HPPD protein and its use for obtaining plants which are tolerant to HPPD inhibitor herbicides is disclosed. Further mutants of the Pseudomonas fluorescens HPPD protein comprising mutations at various sites and their ability to confer resistance to certain HPPD inhibitor herbicides are described in the PCT application filed (on Sep. 13, 2013) under the PCT application number PCT/US2013/59598 and claiming priorities of U.S. 61/701,037 (filed on Sep. 14, 2012), U.S. 61/766,057 (filed on Feb. 18, 2013), and U.S. 61/790,404 (filed in Mar. 15, 2013).

Some of these mutants, i.e. mutants of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed herein under SEQ ID No:6 in PCT/US2013/59598), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598), or (iii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598) are hereby incorporated by reference concerning the production of the respective transgenic plants conferring tolerance to HPPD inhibitor herbicides under its abbreviations PfHPPDEvo33, PfHPPDEvo40, and PfHPPDEvo41, respectively.

In the before, the amino acid named first characterizes the amino acid being present in the wild-type Pseudomonas fluorescens HPPD protein and the character given in the brackets identifies the respective amino acid in the 3 letter code, whereas the character given in front of the brackets identifies the respective amino acid in the 1 letter code.

In WO 04/024928, the inventors have sought to increase the prenylquinone biosynthesis (e.g., synthesis of plastoquinones, tocopherols) in the cells of plants by increasing the flux of the HPP precursor into the cells of these plants. This has been done by connecting the synthesis of said precursor to the “shikimate” pathway by overexpression of the prephenate-dehydrogenase (PDH). They have also noted that the transformation of plants with a gene encoding a PDH enzyme makes it possible to increase the tolerance of said plants to HPPD inhibitors.

In WO 2002/046387, a gene obtained from Avena sativa encoding an HPPD was described to generate plants overexpressing such gene and thereby causing tolerance to various HPPD-inhibitor herbicides.

In WO 2008/150473, the combination of two distinct tolerance mechanisms—a modified Avena sativa gene coding for a mutant HPPD enzyme and a CYP450 Maize monooxygenase (nsf1 gene)—was exemplified in order to obtain an improved tolerance to HPPD inhibitor herbicides, but no data have been disclosed demonstrating the synergistic effects based on the combination of both proteins.

In WO 2010/085705, several mutants of the Avena sativa HPPD were described as well as plants comprising genes encoding such mutated HPPD and thereby causing an increased tolerance to various HPPD-inhibitor herbicides compared to non-mutated HPPD.

In WO 2012/021785, several mutants along HPPD proteins of various organisms, preferably HPPD obtained from maize were described. Data were obtained from such mutated HPPD enzymes in vitro as well as from plants comprising genes encoding such mutated HPPD and thereby causing an increased tolerance to various HPPD-inhibitor herbicides compared to non-mutated HPPD.

Recently, several new genes encoding HPPD enzymes from various organisms have been identified and employed for obtaining crop plants that show an agronomically useful level of tolerance concerning the application of various HPPD inhibitor herbicides, like such (i) obtained from bacteria belonging to the subfamily Synechococcoideae and certain mutants thereof as disclosed in WO2011/076877(PCT/EP2010/070561), (ii) obtained from protists belonging to the family Blepharismidae as disclosed in WO2011/076882 (PCT/EP2010/070567); (iii) obtained from bacteria belonging to the genus Rhodococcus and certain mutants thereof as disclosed in WO2011/076892 (PCT/EP2010/070578); (iv) obtained from Euryarchaeota belonging to the family Picrophilaceae and certain mutants thereof as disclosed in WO2011/076885 (PCT/EP2010/070570); or (v) obtained from bacteria belonging to the genus Kordia and certain mutants thereof disclosed as in WO2011/076889 (PCT/EP2010/070575) and which are hereby incorporated by reference concerning the production of the respective transgenic plants conferring tolerance to HPPD inhibitor herbicides.

SUMMARY

It has now been found that N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides or salts thereof can be employed on transgenic crop plants being tolerant to HPPD inhibitor herbicides by containing one or more genes conferring tolerance to HPPD inhibitor herbicides.

Subject matter of the present invention is the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides of the formula (I) or their salts

in which the substituents are defined as follows:

-   A is N or CY, -   R is hydrogen, (C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, CH₂R⁶,     (C₃-C₇)-cycloalkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,     halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, OR¹,     NHR¹, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,     ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl,     dimethylamino, acetylamino, methylsulfenyl, methylsulfinyl,     methylsulfonyl, or heteroaryl, heterocyclyl, benzyl or phenyl each     substituted by s radicals from the group of halogen, nitro, cyano,     (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,     S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,     (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, -   X is nitro, halogen, cyano, formyl, thiocyanato, (C₁-C₆)-alkyl,     halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,     (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,     halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹,     NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹, OR¹,     OCOR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,     (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,     (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,     (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,     (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², NR¹R², P(O)(OR⁵)₂,     CH₂P(O)(OR⁵)₂, (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl,     where the two latter radicals are each substituted by s halogen,     (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl,     (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy radicals, and where heterocyclyl     bears n oxo groups, -   Y is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,     halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl,     (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹,     NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, CO(NOR¹)R¹,     NR¹SO₂R², NR¹COR¹, OR¹, OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂,     (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,     (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-CN,     (C₁-C₆)-alkyl-SO₂OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,     (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,     (C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂, CH₂P(O)(OR⁵)₂,     (C₁-C₆)-alkylphenyl, (C₁-C₆)-alkylheteroaryl,     (C₁-C₆)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where     the 6 latter radicals are each substituted by s radicals from the     group of halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,     (C₃-C₆)-cycloalkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,     halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl,     and where heterocyclyl bears n oxo groups, -   Z is hydrogen, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl,     (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,     halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₂-C₆)-alkynyl,     (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, COR¹, COOR¹, OCOOR¹,     NR¹COOR¹, C(O)N(R¹)₂, NR¹C(O)N(R¹)₂, OC(O)N(R¹)₂, C(O)NR¹OR¹,     OSO₂R², S(O)_(n)R², SO₂OR¹, SO₂N(R¹)₂, NR¹SO₂R², NR¹COR¹,     (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-OCOR¹,     (C₁-C₆)-alkyl-OSO₂R², (C₁-C₆)-alkyl-CO₂R¹, (C₁-C₆)-alkyl-SO₂OR¹,     (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,     (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R², N(R¹)₂, P(O)(OR⁵)₂,     heteroaryl, heterocyclyl or phenyl, where the three latter radicals     are each substituted by s radicals from the group of halogen, nitro,     cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,     S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or halo-(C₁-C₆)-alkoxy, and     where heterocyclyl bears n oxo groups, -   R¹ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,     (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl,     heterocyclyl, (C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,     (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,     (C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals are     substituted by s radicals from the group consisting of cyano,     halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³,     OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and     (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears     n oxo groups, -   R² is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, (C₃-C₆)-halocycloalkyl,     (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, (C₁-C₆)-alkylheteroaryl,     heterocyclyl, (C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,     (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl,     (C₁-C₆)-alkyl-NR³-heterocyclyl, where the 21 latter radicals are     substituted by s radicals from the group consisting of cyano,     halogen, nitro, thiocyanato, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³,     OCOR³, SCOR⁴, NR³COR³, NR³SO₂R⁴, CO₂R³, COSR⁴, CON(R³)₂ and     (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears     n oxo groups, -   R³ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, -   R⁴ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, -   R⁵ is methyl or ethyl, -   R⁶ is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido,     N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl,     methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl,     trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl,     dimethylaminocarbonyl, (C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl, or     heteroaryl, heterocyclyl or phenyl each substituted by s radicals     from the group of methyl, ethyl, methoxy, trifluoromethyl and     halogen, -   n is 0, 1 or 2; and -   s is 0, 1, 2 or 3.     for controlling unwanted plants in areas of transgenic crop plants     being tolerant to HPPD inhibitor herbicides by containing one or     more chimeric gene(s) (I) comprising a DNA sequence encoding     hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a     group of organisms consisting of (a) Avena, preferably Avena sativa,     more preferably comprising a DNA sequence identical to SEQ ID No. 1     encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably     Pseudomonas fluorescens, more preferably comprising a DNA sequence     identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c)     Synechococcoideae, preferably Synechococcus sp., more preferably     comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD     defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma     japonicum, more preferably comprising a DNA sequence identical to     SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus,     preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more     preferably comprising a DNA sequence identical to SEQ ID No. 10     encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain     RHA1), isolate ro02040, more preferably comprising a DNA sequence     identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No.     13, (f) Picrophilaceae, preferably Picrophilus torridus, more     preferably comprising a DNA sequence identical to SEQ ID No. 14     encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably     Kordia algicida, more preferably comprising a DNA sequence identical     to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II)     comprising one or more mutated DNA sequences of HPPD encoding genes     of the before defined organisms, preferably mutants as described in     WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079,     WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885,     WO2011/076889, WO 2012/021785, according to the latter, comprising     more especially one or more mutated DNA sequences of HPPD encoding     genes obtained from maize (Zea mays) or soybean (Glycine max),     especially preferable HPPD encoding genes from maize (Zea mays) or     (Ill) comprising a mutated DNA sequence described in     PCT/US2013/59598, more specifically a mutated sequence of the     Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P     (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement     at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID     No:6 in PCT/US2013/59598 and being disclosed in present application     under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro)     replacement at position 335, a G (Gly)->S (Ser) replacement at     position 336, and an A (Ala)->E (Glu) replacement at position 340     (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in     PCT/US2013/59598 and being disclosed in present application under     SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement     at position 335, a G (Gly)->W (Trp) replacement at position 336, a K     (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln)     replacement at position 340 (named PfHPPDEvo41 and being disclosed     under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in     present application under SEQ ID No. 29), or (IV) comprising a     mutated DNA sequence described in PCT/US2013/59598, more     specifically a mutated sequence of the Pseudomonas (=Comamonas)     testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro)     replacement at position 351, a G (Gly)->S (Ser) replacement at     position 352, and an A (Ala)->E (Glu) replacement at position 356     (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in     PCT/US2013/59598, and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 32), (ii) comprising a E     (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp)     replacement at position 352, a K (Lys)->A (Ala) replacement at     position 355 and an A (Ala)->Q (Gln) replacement at position 356     (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in     PCT/US2013/59598 and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 33), or (V) comprising a     mutated DNA sequence described in PCT/US2013/59598, more     specifically a mutated sequence of the Pseudomonas aeruginosa strain     ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at     position 337, a G (Gly)->S (Ser) replacement at position 338, and an     A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40     and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and     being disclosed in present application as the HPPD protein sequence     under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement     at position 337, a G (Gly)->W (Trp) replacement at position 338, a K     (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln)     replacement at position 342 (named Axmi305H-Evo41 and being     disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed     in present application as the HPPD protein sequence under SEQ ID No     41), or (VI) comprising a mutated DNA sequence described in     PCT/US2013/59598, more specifically a mutated sequence of the     Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro)     replacement at position 335, a G (Gly)->S (Ser) replacement at     position 336, and an A (Ala)->E (Glu) replacement at position 340     (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in     PCT/US2013/59598, and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 36), (ii) comprising a E     (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp)     replacement at position 336, a K (Lys)->A (Ala) replacement at     position 339 and an A (Ala)->Q (Gln) replacement at position 340     (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in     PCT/US2013/59598 and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 37).

In the formula (I) and all the formulae which follow, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, tert- or 2-butyl, pentyls, hexyls such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, semi saturated or fully unsaturated cyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,

Heteroaryl is an aromatic cyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are from the group of oxygen, nitrogen and sulfur, and which may additionally be fused by a benzo ring. For example, heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

When a group is polysubstituted by radicals, this means that this group is substituted by one or more identical or different radicals from those mentioned.

According to the nature and the bonding of the substituents, the compounds of the general formula (I) may be present as stereoisomers. When, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers likewise occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation processes. It is equally possible to selectively prepare stereoisomers by using stereo selective reactions using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers and mixtures thereof which are encompassed by the general formula (I) but not defined specifically.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Preference is given to the inventive use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides of general formula (I), in which

-   A is N or CY, -   R is hydrogen, (C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl,     halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkylmethyl, methoxycarbonylmethyl,     ethoxycarbonylmethyl, acetylmethyl, methoxymethyl, methoxyethyl,     benzyl, pyrazin-2-yl, furan-2-yl, tetrahydrofuran-2-yl, morpholine,     dimethylamino, or phenyl substituted by s radicals from the group of     methyl, methoxy, trifluoromethyl and halogen; -   X is nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,     (C₃-C₆)-cycloalkyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,     (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂, (C₁-C₆)-alkyl-SO₂N(R¹)₂,     (C₁-C₆)-alkyl-NR¹COR¹, (C₁-C₆)-alkyl-NR¹SO₂R²,     (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, where the two     latter radicals are each substituted by s halogen, (C₁-C₆)-alkyl,     halo-(C₁-C₆)-alkyl, S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,     halo-(C₁-C₆)-alkoxy radicals, and where heterocyclyl bears n oxo     groups, -   Y hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,     OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R², NR¹COR¹,     (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,     (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,     (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylphenyl,     (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, phenyl,     heteroaryl or heterocyclyl, where the 6 latter radicals are each     substituted by s radicals from the group of halogen, nitro, cyano,     (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,     S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,     (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclyl     bears n oxo groups, -   Z is halogen, cyano, nitro, methyl, halo-(C₁-C₆)-alkyl,     (C₃-C₆)-cycloalkyl, S(O)_(n)R², 1,2,4-triazol-1-yl, pyrazol-1-yl, or     -   Z may also be hydrogen if Y is the S(O)_(n)R² radical, -   R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,     heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,     (C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,     (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or     (C₁-C₆)-alkyl-NR³-heterocyclyl, where the 16 latter radicals are     substituted by s radicals from the group consisting of cyano,     halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³,     NR³COR³, NR³SO₂R⁴, CO₂R³, —CON(R³)₂ and     (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears     n oxo groups, -   R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where these three aforementioned     radicals are each substituted by s radicals from the group     consisting of halogen and OR³, -   R³ is hydrogen or (C₁-C₆)-alkyl, -   R⁴ is (C₁-C₆)-alkyl, -   n is 0, 1 or 2; -   s is 0, 1, 2 or 3,     for controlling unwanted plants in areas of transgenic crop plants     being tolerant to HPPD inhibitor herbicides by containing one or     more chimeric gene(s) (I) comprising a DNA sequence encoding     hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a     group of organisms consisting of (a) Avena, preferably Avena sativa,     more preferably comprising a DNA sequence identical to SEQ ID No. 1     encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably     Pseudomonas fluorescens, more preferably comprising a DNA sequence     identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c)     Synechococcoideae, preferably Synechococcus sp., more preferably     comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD     defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma     japonicum, more preferably comprising a DNA sequence identical to     SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus,     preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more     preferably comprising a DNA sequence identical to SEQ ID No. 10     encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain     RHA1), isolate ro02040, more preferably comprising a DNA sequence     identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No.     13, (f) Picrophilaceae, preferably Picrophilus torridus, more     preferably comprising a DNA sequence identical to SEQ ID No. 14     encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably     Kordia algicida, more preferably comprising a DNA sequence identical     to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II)     comprising one or more mutated DNA sequences of HPPD encoding genes     of the before defined organisms, preferably mutants as described in     WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079,     WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885,     WO2011/076889, WO 2012/021785, according to the latter, comprising     more especially one or more mutated DNA sequences of HPPD encoding     genes obtained from maize (Zea mays) or soybean (Glycine max),     especially preferable HPPD encoding genes from maize (Zea mays) or     (Ill) comprising a mutated DNA sequence described in     PCT/US2013/59598, more specifically a mutated sequence of the     Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P     (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement     at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID     No:6 in PCT/US2013/59598 and being disclosed in present application     under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro)     replacement at position 335, a G (Gly)->S (Ser) replacement at     position 336, and an A (Ala)->E (Glu) replacement at position 340     (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in     PCT/US2013/59598 and being disclosed in present application under     SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement     at position 335, a G (Gly)->W (Trp) replacement at position 336, a K     (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln)     replacement at position 340 (named PfHPPDEvo41 and being disclosed     under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in     present application under SEQ ID No. 29), or (IV) comprising a     mutated DNA sequence described in PCT/US2013/59598, more     specifically a mutated sequence of the Pseudomonas (=Comamonas)     testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro)     replacement at position 351, a G (Gly)->S (Ser) replacement at     position 352, and an A (Ala)->E (Glu) replacement at position 356     (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in     PCT/US2013/59598, and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 32), (ii) comprising a E     (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp)     replacement at position 352, a K (Lys)->A (Ala) replacement at     position 355 and an A (Ala)->Q (Gln) replacement at position 356     (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in     PCT/US2013/59598 and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 33), or (V) comprising a     mutated DNA sequence described in PCT/US2013/59598, more     specifically a mutated sequence of the Pseudomonas aeruginosa strain     ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at     position 337, a G (Gly)->S (Ser) replacement at position 338, and an     A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40     and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and     being disclosed in present application as the HPPD protein sequence     under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement     at position 337, a G (Gly)->W (Trp) replacement at position 338, a K     (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln)     replacement at position 342 (named Axmi305H-Evo41 and being     disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed     in present application as the HPPD protein sequence under SEQ ID No     41), or (VI) comprising a mutated DNA sequence described in     PCT/US2013/59598, more specifically a mutated sequence of the     Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro)     replacement at position 335, a G (Gly)->S (Ser) replacement at     position 336, and an A (Ala)->E (Glu) replacement at position 340     (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in     PCT/US2013/59598, and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 36), (ii) comprising a E     (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp)     replacement at position 336, a K (Lys)->A (Ala) replacement at     position 339 and an A (Ala)->Q (Gln) replacement at position 340     (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in     PCT/US2013/59598 and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 37).

Particular preference is given to the inventive use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides of general formula (I), in which

-   A is N or CY, -   R is hydrogen, (C₁-C₄)-alkyl, cyclopropyl, halo-(C₁-C₄)-alkyl,     (C₃-C₆)-cycloalkylmethyl, methoxymethyl, methoxyethyl, benzyl; -   X is nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,     cyclopropyl, OR¹, S(O)_(n)R², (C₁-C₆)-alkyl-S(O)_(n)R²,     (C₁-C₆)-alkyl-OR¹, (C₁-C₂)-alkylheteroaryl,     (C₁-C₂)-alkylheterocyclyl, where the two latter radicals are each     substituted by s halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl,     S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy     radicals, and where heterocyclyl bears n oxo groups, -   Y hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,     OR¹, S(O)_(n)R², SO₂N(R¹)₂, N(R¹)₂, NR¹SO₂R², NR¹COR¹,     (C₁-C₆)-alkyl-S(O)_(n)R², (C₁-C₆)-alkyl-OR¹, (C₁-C₆)-alkyl-CON(R¹)₂,     (C₁-C₆)-alkyl-SO₂N(R¹)₂, (C₁-C₆)-alkyl-NR¹COR¹,     (C₁-C₆)-alkyl-NR¹SO₂R², (C₁-C₆)-alkylphenyl,     (C₁-C₆)-alkylheteroaryl, (C₁-C₆)-alkylheterocyclyl, phenyl,     heteroaryl or heterocyclyl, where the 6 latter radicals are each     substituted by s radicals from the group of halogen, nitro, cyano,     (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,     S(O)_(n)—(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy,     (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl and cyanomethyl, and where heterocyclyl     bears n oxo groups, -   Z is halogen, cyano, nitro, methyl, halo-(C₁-C₆)-alkyl,     (C₃-C₆)-cycloalkyl, S(O)_(n)R², 1,2,4-triazol-1-yl, pyrazol-1-yl, -   R¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,     (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl,     heteroaryl, (C₁-C₆)-alkylheteroaryl, heterocyclyl,     (C₁-C₆)-alkylheterocyclyl, (C₁-C₆)-alkyl-O-heteroaryl,     (C₁-C₆)-alkyl-O-heterocyclyl, (C₁-C₆)-alkyl-NR³-heteroaryl or     (C₁-C₆)-alkyl-NR³-heterocyclyl, where the 16 latter radicals are     substituted by s radicals from the group consisting of cyano,     halogen, nitro, OR³, S(O)_(n)R⁴, N(R³)₂, NR³OR³, COR³, OCOR³,     NR³COR³, NR³SO₂R⁴, CO₂R³, —CON(R³)₂ and     (C₁-C₄)-alkoxy-(C₂-C₆)-alkoxycarbonyl, and where heterocyclyl bears     n oxo groups, -   R² is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl or     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where these three aforementioned     radicals are each substituted by s radicals from the group     consisting of halogen and OR³, -   R³ is hydrogen or (C₁-C₆)-alkyl, -   R⁴ is (C₁-C₆)-alkyl, -   n is 0, 1 or 2; -   s is 0, 1, 2 or 3,     for controlling unwanted plants in areas of transgenic crop plants     being tolerant to HPPD inhibitor herbicides by containing one or     more chimeric gene(s) (I) comprising a DNA sequence encoding     hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a     group of organisms consisting of (a) Avena, preferably Avena sativa,     more preferably comprising a DNA sequence identical to SEQ ID No. 1     encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably     Pseudomonas fluorescens, more preferably comprising a DNA sequence     identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c)     Synechococcoideae, preferably Synechococcus sp., more preferably     comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD     defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma     japonicum, more preferably comprising a DNA sequence identical to     SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus,     preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more     preferably comprising a DNA sequence identical to SEQ ID No. 10     encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain     RHA1), isolate ro02040, more preferably comprising a DNA sequence     identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No.     13, (f) Picrophilaceae, preferably Picrophilus torridus, more     preferably comprising a DNA sequence identical to SEQ ID No. 14     encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably     Kordia algicida, more preferably comprising a DNA sequence identical     to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II)     comprising one or more mutated DNA sequences of HPPD encoding genes     of the before defined organisms, preferably mutants as described in     WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079,     WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885,     WO2011/076889, WO 2012/021785, according to the latter, comprising     more especially one or more mutated DNA sequences of HPPD encoding     genes obtained from maize (Zea mays) or soybean (Glycine max),     especially preferable HPPD encoding genes from maize (Zea mays) or     (Ill) comprising a mutated DNA sequence described in     PCT/US2013/59598, more specifically a mutated sequence of the     Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P     (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement     at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID     No:6 in PCT/US2013/59598 and being disclosed in present application     under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro)     replacement at position 335, a G (Gly)->S (Ser) replacement at     position 336, and an A (Ala)->E (Glu) replacement at position 340     (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in     PCT/US2013/59598 and being disclosed in present application under     SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement     at position 335, a G (Gly)->W (Trp) replacement at position 336, a K     (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln)     replacement at position 340 (named PfHPPDEvo41 and being disclosed     under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in     present application under SEQ ID No. 29), or (IV) comprising a     mutated DNA sequence described in PCT/US2013/59598, more     specifically a mutated sequence of the Pseudomonas (=Comamonas)     testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro)     replacement at position 351, a G (Gly)->S (Ser) replacement at     position 352, and an A (Ala)->E (Glu) replacement at position 356     (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in     PCT/US2013/59598, and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 32), (ii) comprising a E     (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp)     replacement at position 352, a K (Lys)->A (Ala) replacement at     position 355 and an A (Ala)->Q (Gln) replacement at position 356     (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in     PCT/US2013/59598 and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 33), or (V) comprising a     mutated DNA sequence described in PCT/US2013/59598, more     specifically a mutated sequence of the Pseudomonas aeruginosa strain     ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at     position 337, a G (Gly)->S (Ser) replacement at position 338, and an     A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40     and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and     being disclosed in present application as the HPPD protein sequence     under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement     at position 337, a G (Gly)->W (Trp) replacement at position 338, a K     (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln)     replacement at position 342 (named Axmi305H-Evo41 and being     disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed     in present application as the HPPD protein sequence under SEQ ID No     41), or (VI) comprising a mutated DNA sequence described in     PCT/US2013/59598, more specifically a mutated sequence of the     Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro)     replacement at position 335, a G (Gly)->S (Ser) replacement at     position 336, and an A (Ala)->E (Glu) replacement at position 340     (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in     PCT/US2013/59598, and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 36), (ii) comprising a E     (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp)     replacement at position 336, a K (Lys)->A (Ala) replacement at     position 339 and an A (Ala)->Q (Gln) replacement at position 340     (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in     PCT/US2013/59598 and being disclosed in present application as the     HPPD protein sequence under SEQ ID No 37).

In all of the formulae below, the substituents and symbols have the same definition as described under formula (I), unless otherwise defined.

N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides to be used according to the invention can be prepared as described in detail in WO2012/126932 which is hereby incorporated by reference.

The compounds listed in the Tables 1 to 7, herein below, are very specially preferred used for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor herbicides by containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

The abbreviations used mean:

-   -   Et=ethyl Me=methyl n-Pr=n-propyl i-Pr=isopropyl     -   c-Pr=cyclopropyl Ph=phenyl Ac=acetyl Bz=benzoyl

TABLE 1 Compounds of the general formula (I) in which A is CY and R is hydrogen and X, Y, and Z are as defined below.

No. X Y Z 1-1 F H Cl 1-2 F H SO₂Me 1-3 F H SO₂Et 1-4 F H CF₃ 1-5 F H NO₂ 1-6 Cl H Br 1-7 Cl H SMe 1-8 Cl H SOMe 1-9 Cl H SO₂Me 1-10 Cl H SO₂CH₂Cl 1-11 Cl H SEt 1-12 Cl H SO₂Et 1-13 Cl H CF₃ 1-14 Cl H NO₂ 1-15 Cl H pyrazol-1-yl 1-16 Cl H 1H-1,2,4- triazol-1-yl 1-17 Br H Cl 1-18 Br H Br 1-19 Br H SO₂Me 1-20 Br H SO₂Et 1-21 Br H CF₃ 1-22 SO₂Me H Cl 1-23 SO₂Me H Br 1-24 SO₂Me H SMe 1-25 SO₂Me H SOMe 1-26 SO₂Me H SO₂Me 1-27 SO₂Me H SO₂Et 1-28 SO₂Me H CF₃ 1-29 SO₂Et H Cl 1-30 SO₂Et H Br 1-31 SO₂Et H SMe 1-32 SO₂Et H SOMe 1-33 SO₂Et H SO₂Me 1-34 SO₂Et H CF₃ 1-35 NO₂ H F 1-36 NO₂ H Cl 1-37 NO₂ H Br 1-38 NO₂ H I 1-39 NO₂ H CN 1-40 NO₂ H SO₂Me 1-41 NO₂ H SO₂Et 1-42 NO₂ H CF₃ 1-43 Me H Cl 1-44 Me H Br 1-45 Me H SMe 1-46 Me H SO₂Me 1-47 Me H SO₂CH₂Cl 1-48 Me H SEt 1-49 Me H SO₂Et 1-50 Me H CF₃ 1-51 CH₂SO₂Me H CF₃ 1-52 Et H Cl 1-53 Et H Br 1-54 Et H SMe 1-55 Et H SO₂Me 1-56 Et H SO₂CH₂Cl 1-57 Et H SEt 1-58 Et H SO₂Et 1-59 Et H CF₃ 1-60 CF₃ H Cl 1-61 CF₃ H Br 1-62 CF₃ H SO₂Me 1-63 CF₃ H SO₂Et 1-64 CF₃ H CF₃ 1-65 NO₂ NH₂ F 1-66 NO₂ NHMe F 1-67 NO₂ NMe₂ F 1-68 NO₂ Me Cl 1-69 NO₂ NH₂ Cl 1-70 NO₂ NHMe Cl 1-71 NO₂ NMe₂ Cl 1-72 NO₂ NH₂ Br 1-73 NO₂ NHMe Br 1-74 NO₂ NMe₂ Br 1-75 NO₂ NH₂ CF₃ 1-76 NO₂ NMe₂ CF₃ 1-77 NO₂ NH₂ SO₂Me 1-78 NO₂ NH₂ SO₂Et 1-79 NO₂ NHMe SO₂Me 1-80 NO₂ NMe₂ SO₂Me 1-81 NO₂ NMe₂ SO₂Et 1-82 NO₂ NH₂ 1H-1,2,4- triazol-1-yl 1-83 NO₂ NHMe 1H-1,2,4- triazol-1-yl 1-84 NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 1-85 Me SMe H 1-86 Me SOMe H 1-87 Me SO₂Me H 1-88 Me SEt H 1-89 Me SOEt H 1-90 Me SO₂Et H 1-91 Me S(CH₂)₂OMe H 1-92 Me SO(CH₂)₂OMe H 1-93 Me SO₂(CH₂)₂OMe H 1-94 Me F F 1-95 Me F Cl 1-96 Me SEt F 1-97 Me SOEt F 1-98 Me SO₂Et F 1-99 Me Me Cl 1-100 Me F Cl 1-101 Me Cl Cl 1-102 Me NH₂ Cl 1-103 Me NHMe Cl 1-104 Me NMe₂ Cl 1-105 Me O(CH₂)₂OMe Cl 1-106 Me O(CH₂)₃OMe Cl 1-107 Me O(CH₂)₄OMe Cl 1-108 Me OCH₂CONMe₂ Cl 1-109 Me O(CH₂)₂—CO—NMe₂ Cl 1-110 Me O(CH₂)₂— Cl NH(CO)NMe₂ 1-111 Me O(CH₂)₂— Cl NH(CO)NHCO₂Et 1-112 Me O(CH₂)₂—NHCO₂Me Cl 1-113 Me OCH₂—NHSO₂cPr Cl 1-114 Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H-1,2,4- triazol-3-one 1-115 Me O(CH₂)-3,5- Cl dimethyl-1,2-oxazol- 4-yl 1-116 Me SMe Cl 1-117 Me SOMe Cl 1-118 Me SO₂Me Cl 1-119 Me SEt Cl 1-120 Me SOEt Cl 1-121 Me SO₂Et Cl 1-122 Me S(CH₂)₂OMe Cl 1-123 Me SO(CH₂)₂OMe Cl 1-124 Me SO₂(CH₂)₂OMe Cl 1-125 Me NH₂ Br 1-126 Me NHMe Br 1-127 Me NMe₂ Br 1-128 Me OCH₂(CO)NMe₂ Br 1-129 Me O(CH₂)-5-pyrrolidin- Br 2-one 1-130 Me SMe Br 1-131 Me SOMe Br 1-132 Me SO₂Me Br 1-133 Me SEt Br 1-134 Me SOEt Br 1-135 Me SO₂Et Br 1-136 Me SMe I 1-137 Me SOMe I 1-138 Me SO₂Me I 1-139 Me SEt I 1-140 Me SOEt I 1-141 Me SO₂Et I 1-142 Me Cl CF₃ 1-143 Me SMe CF₃ 1-144 Me SOMe CF₃ 1-145 Me SO₂Me CF₃ 1-146 Me SEt CF₃ 1-147 Me SOEt CF₃ 1-148 Me SO₂Et CF₃ 1-149 Me S(CH₂)₂OMe CF₃ 1-150 Me SO(CH₂)₂OMe CF₃ 1-151 Me SO₂(CH₂)₂OMe CF₃ 1-152 Me Me SO₂Me 1-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 1-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 1-157 Me NH₂ SO₂Me 1-158 Me NHMe SO₂Me 1-159 Me NMe₂ SO₂Me 1-160 Me NH(CH₂)₂OMe SO₂Me 1-161 Me pyrazol-1-yl SO₂Me 1-162 Me OH SO₂Me 1-163 Me OMe SO₂Me 1-164 Me OMe SO₂Et 1-165 Me OEt SO₂Me 1-166 Me OEt SO₂Et 1-167 Me OiPr SO₂Me 1-168 Me OiPr SO₂Et 1-169 Me O(CH₂)₂OMe SO₂Me 1-170 Me O(CH₂)₂OMe SO₂Et 1-171 Me O(CH₂)₃OMe SO₂Me 1-172 Me O(CH₂)₃OMe SO₂Et 1-173 Me O(CH₂)₄OMe SO₂Me 1-174 Me O(CH₂)₄OMe SO₂Et 1-175 Me O(CH₂)₂NHSO2Me SO₂Me 1-176 Me O(CH₂)₂NHSO2Me SO₂Et 1-177 Me OCH₂(CO)NMe₂ SO₂Me 1-178 Me OCH₂(CO)NMe₂ SO₂Et 1-179 Me [1,4]dioxan-2-yl- SO₂Me methoxy 1-180 Me [1,4]dioxan-2-yl- SO₂Et methoxy 1-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2- yl) 1-182 Me Cl SO₂Me 1-183 Me SMe SO₂Me 1-184 Me SOMe SO₂Me 1-185 Me SO₂Me SO₂Me 1-186 Me SO₂Me SO₂Et 1-187 Me SEt SO₂Me 1-188 Me SOEt SO₂Me 1-189 Me SO₂Et SO₂Me 1-190 Me S(CH₂)₂OMe SO₂Me 1-191 Me SO(CH₂)₂OMe SO₂Me 1-192 Me SO₂(CH₂)₂OMe SO₂Me 1-193 CH₂SMe OMe SO₂Me 1-194 CH₂OMe OMe SO₂Me 1-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 1-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 1-197 CH₂O(CH₂)₃OMe OMe SO₂Me 1-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 1-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 1-200 Et SMe Cl 1-201 Et SO₂Me Cl 1-202 Et SMe CF₃ 1-203 Et SO₂Me CF₃ 1-204 Et F SO₂Me 1-205 Et NH(CH₂)₂OMe SO₂Me 1-206 iPr SO₂Me CF₃ 1-207 cPr SO₂Me CF₃ 1-208 CF₃ O(CH₂)₂OMe F 1-209 CF₃ O(CH₂)₃OMe F 1-210 CF₃ OCH₂CONMe₂ F 1-211 CF₃ [1,4]dioxan-2-yl- F methoxy 1-212 CF₃ O(CH₂)₂OMe Cl 1-213 CF₃ O(CH₂)₃OMe Cl 1-214 CF₃ OCH₂CONMe₂ Cl 1-215 CF₃ [1,4]dioxan-2-yl- Cl methoxy 1-216 CF₃ O(CH₂)₂OMe Br 1-217 CF₃ O(CH₂)₃OMe Br 1-218 CF₃ OCH₂CONMe₂ Br 1-219 CF₃ [1,4]dioxan-2-yl- Br methoxy 1-220 CF₃ O(CH₂)₂OMe I 1-221 CF₃ O(CH₂)₃OMe I 1-222 CF₃ OCH₂CONMe₂ I 1-223 CF₃ [1,4]dioxan-2-yl- I methoxy 1-224 CF₃ F SO₂Me 1-225 CF₃ F SO₂Et 1-226 CF₃ O(CH₂)₂OMe SO₂Me 1-227 CF₃ O(CH₂)₂OMe SO₂Et 1-228 CF₃ O(CH₂)₃OMe SO₂Me 1-229 CF₃ O(CH₂)₃OMe SO₂Et 1-230 CF₃ OCH₂CONMe₂ SO₂Me 1-231 CF₃ OCH₂CONMe₂ SO₂Et 1-232 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 1-233 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 1-234 F SMe CF₃ 1-235 F SOMe CF₃ 1-236 Cl Me Cl 1-237 Cl OCH₂CHCH₂ Cl 1-238 Cl OCH₂CHF₂ Cl 1-239 Cl O(CH₂)₂OMe Cl 1-240 Cl OCH₂CONMe₂ Cl 1-241 Cl O(CH₂)-5-pyrrolidin- Cl 2-one 1-242 Cl SMe Cl 1-243 Cl SOMe Cl 1-244 Cl SO₂Me Cl 1-245 Cl F SMe 1-246 Cl Cl SO₂Me 1-247 Cl COOMe SO₂Me 1-248 Cl CONMe₂ SO₂Me 1-249 Cl CONMe(OMe) SO₂Me 1-250 Cl CH₂OMe SO₂Me 1-251 Cl CH₂OMe SO₂Et 1-252 Cl CH₂OEt SO₂Me 1-253 Cl CH₂OEt SO₂Et 1-254 Cl CH₂OCH₂CHF₂ SO₂Me 1-255 Cl CH₂OCH₂CF₃ SO₂Me 1-256 Cl CH₂OCH₂CF₃ SO₂Et 1-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 1-258 Cl CH₂OcPentyl SO₂Me 1-259 Cl CH₂PO(OMe)₂ SO₂Me 1-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 1-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 1-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 1-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 1-264 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 1-265 Cl 5-(methoxymethyl)- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 1-266 Cl 5-(methoxymethyl)- SO₂Et 5-methyl-4,5- dihydro-1,2-oxazol- 3-yl 1-267 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 1-268 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 1-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 1-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 1-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 1-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 1-273 Cl OMe SO₂Me 1-274 Cl OMe SO₂Et 1-275 Cl OEt SO₂Me 1-276 Cl OEt SO₂Et 1-277 Cl OiPr SO₂Me 1-278 Cl OiPr SO₂Et 1-279 Cl O(CH₂)₂OMe SO₂Me 1-280 Cl O(CH₂)₄OMe SO₂Me 1-281 Cl O(CH₂)₄OMe SO₂Et 1-282 Cl O(CH₂)₃OMe SO₂Me 1-283 Cl O(CH₂)₃OMe SO₂Et 1-284 Cl O(CH₂)₂OMe SO₂Me 1-285 Cl O(CH₂)₂OMe SO₂Et 1-286 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 1-287 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 1-288 Cl OCH₂(CO)NMe₂ SO₂Me 1-289 Cl OCH₂(CO)NMe₂ SO₂Et 1-290 Cl SMe SO₂Me 1-291 Cl SOMe SO₂Me 1-292 Br OMe Br 1-293 Br O(CH₂)₂OMe Br 1-294 Br O(CH₂)₂OMe SO₂Me 1-295 Br O(CH₂)₂OMe SO₂Et 1-296 Br O(CH₂)₃OMe SO₂Me 1-297 Br O(CH₂)₃OMe SO₂Et 1-298 Br O(CH₂)₄OMe SO₂Me 1-299 Br O(CH₂)₄OMe SO₂Et 1-300 Br [1,4]dioxan-2-yl- SO₂Me methoxy 1-301 Br [1,4]dioxan-2-yl- SO₂Et methoxy 1-302 I O(CH₂)₂OMe SO₂Me 1-303 I O(CH₂)₂OMe SO₂Et 1-304 I O(CH₂)₃OMe SO₂Me 1-305 I O(CH₂)₃OMe SO₂Et 1-306 I O(CH₂)₄OMe SO₂Me 1-307 I O(CH₂)₄OMe SO₂Et 1-308 I [1,4]dioxan-2-yl- SO₂Me methoxy 1-309 I [1,4]dioxan-2-yl- SO₂Et methoxy 1-310 OMe SMe CF₃ 1-311 OMe SOMe CF₃ 1-312 OMe SO₂Me CF₃ 1-313 OMe SOEt CF₃ 1-314 OMe SO₂Et CF₃ 1-315 OMe S(CH₂)₂OMe CF₃ 1-316 OMe SO(CH₂)₂OMe CF₃ 1-317 OMe SO₂(CH₂)₂OMe CF₃ 1-318 OMe SMe Cl 1-319 OMe SOMe Cl 1-320 OMe SO₂Me Cl 1-321 OMe SEt Cl 1-322 OMe SOEt Cl 1-323 OMe SO₂Et Cl 1-324 OMe S(CH₂)₂OMe Cl 1-325 OMe SO(CH₂)₂OMe Cl 1-326 OMe SO₂(CH₂)₂OMe Cl 1-327 OCH₂c-Pr SMe CF₃ 1-328 OCH₂c-Pr SOMe CF₃ 1-329 OCH₂c-Pr SO₂Me CF₃ 1-330 OCH₂c-Pr SEt CF₃ 1-331 OCH₂c-Pr SOEt CF₃ 1-332 OCH₂c-Pr SO₂Et CF₃ 1-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 1-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 1-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 1-336 OCH₂c-Pr SMe Cl 1-337 OCH₂c-Pr SOMe Cl 1-338 OCH₂c-Pr SO₂Me Cl 1-339 OCH₂c-Pr SEt Cl 1-340 OCH₂c-Pr SOEt Cl 1-341 OCH₂c-Pr SO₂Et Cl 1-342 OCH₂c-Pr S(CH₂)₂OMe Cl 1-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 1-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 1-345 OCH₂c-Pr SMe SO₂Me 1-346 OCH₂c-Pr SOMe SO₂Me 1-347 OCH₂c-Pr SO₂Me SO₂Me 1-348 OCH₂c-Pr SEt SO₂Me 1-349 OCH₂c-Pr SOEt SO₂Me 1-350 OCH₂c-Pr SO₂Et SO₂Me 1-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 1-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 1-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 1-354 SO₂Me F CF₃ 1-355 SO₂Me NH₂ CF₃ 1-356 SO₂Me NHEt Cl 1-357 SMe SEt F 1-358 SMe SMe F 1-359 Cl SMe CF₃ 1-360 Cl S(O)Me CF₃ 1-361 Cl CF₃ CF₃ 1-362 Cl CF₃ CF₃

TABLE 2 Compounds of the general formula (I) in which A is CY and R is methyl, and X, Y, and Z are as defined below.

No. X Y Z 2-1 F H Cl 2-2 F H SO₂Me 2-3 F H SO₂Et 2-4 F H CF₃ 2-5 F H NO₂ 2-6 Cl H Br 2-7 Cl H SMe 2-8 Cl H SOMe 2-9 Cl H SO₂Me 2-10 Cl H SO₂CH₂Cl 2-11 Cl H SEt 2-12 Cl H SO₂Et 2-13 Cl H CF₃ 2-14 Cl H NO₂ 2-15 Cl H pyrazol-1-yl 2-16 Cl H 1H-1,2,4- triazol-1-yl 2-17 Br H Cl 2-18 Br H Br 2-19 Br H SO₂Me 2-20 Br H SO₂Et 2-21 Br H CF₃ 2-22 SO₂Me H Cl 2-23 SO₂Me H Br 2-24 SO₂Me H SMe 2-25 SO₂Me H SOMe 2-26 SO₂Me H SO₂Me 2-27 SO₂Me H SO₂Et 2-28 SO₂Me H CF₃ 2-29 SO₂Et H Cl 2-30 SO₂Et H Br 2-31 SO₂Et H SMe 2-32 SO₂Et H SOMe 2-33 SO₂Et H SO₂Me 2-34 SO₂Et H CF₃ 2-35 NO₂ H F 2-36 NO₂ H Cl 2-37 NO₂ H Br 2-38 NO₂ H I 2-39 NO₂ H CN 2-40 NO₂ H SO₂Me 2-41 NO₂ H SO₂Et 2-42 NO₂ H CF₃ 2-43 Me H Cl 2-44 Me H Br 2-45 Me H SMe 2-46 Me H SO₂Me 2-47 Me H SO₂CH₂Cl 2-48 Me H SEt 2-49 Me H SO₂Et 2-50 Me H CF₃ 2-51 CH₂SO₂Me H CF₃ 2-52 Et H Cl 2-53 Et H Br 2-54 Et H SMe 2-55 Et H SO₂Me 2-56 Et H SO₂CH₂Cl 2-57 Et H SEt 2-58 Et H SO₂Et 2-59 Et H CF₃ 2-60 CF₃ H Cl 2-61 CF₃ H Br 2-62 CF₃ H SO₂Me 2-63 CF₃ H SO₂Et 2-64 CF₃ H CF₃ 2-65 NO₂ NH₂ F 2-66 NO₂ NHMe F 2-67 NO₂ NMe₂ F 2-68 NO₂ Me Cl 2-69 NO₂ NH₂ Cl 2-70 NO₂ NHMe Cl 2-71 NO₂ NMe₂ Cl 2-72 NO₂ NH₂ Br 2-73 NO₂ NHMe Br 2-74 NO₂ NMe₂ Br 2-75 NO₂ NH₂ CF₃ 2-76 NO₂ NMe₂ CF₃ 2-77 NO₂ NH₂ SO₂Me 2-78 NO₂ NH₂ SO₂Et 2-79 NO₂ NHMe SO₂Me 2-80 NO₂ NMe₂ SO₂Me 2-81 NO₂ NMe₂ SO₂Et 2-82 NO₂ NH₂ 1H-1,2,4- triazol-1-yl 2-83 NO₂ NHMe 1H-1,2,4- triazol-1-yl 2-84 NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 2-85 Me SMe H 2-86 Me SOMe H 2-87 Me SO₂Me H 2-88 Me SEt H 2-89 Me SOEt H 2-90 Me SO₂Et H 2-91 Me S(CH₂)₂OMe H 2-92 Me SO(CH₂)₂OMe H 2-93 Me SO₂(CH₂)₂OMe H 2-94 Me F F 2-95 Me F Cl 2-96 Me SEt F 2-97 Me SOEt F 2-98 Me SO₂Et F 2-99 Me Me Cl 2-100 Me F Cl 2-101 Me Cl Cl 2-102 Me NH₂ Cl 2-103 Me NHMe Cl 2-104 Me NMe₂ Cl 2-105 Me O(CH₂)₂OMe Cl 2-106 Me O(CH₂)₃OMe Cl 2-107 Me O(CH₂)₄OMe Cl 2-108 Me OCH₂CONMe₂ Cl 2-109 Me O(CH₂)₂—CO—NMe₂ Cl 2-110 Me O(CH₂)₂— Cl NH(CO)NMe₂ 2-111 Me O(CH₂)₂— Cl NH(CO)NHCO₂Et 2-112 Me O(CH₂)₂—NHCO₂Me Cl 2-113 Me O—CH₂—NHSO₂cPr Cl 2-114 Me O(CH₂)-5-2,4- Cl dimethyl-2,4- dihydro-3H-1,2,4- triazol-3-one 2-115 Me O(CH₂)-3,5- Cl dimethyl-1,2-oxazol- 4-yl 2-116 Me SMe Cl 2-117 Me SOMe Cl 2-118 Me SO₂Me Cl 2-119 Me SEt Cl 2-120 Me SOEt Cl 2-121 Me SO₂Et Cl 2-122 Me S(CH₂)₂OMe Cl 2-123 Me SO(CH₂)₂OMe Cl 2-124 Me SO₂(CH₂)₂OMe Cl 2-125 Me NH₂ Br 2-126 Me NHMe Br 2-127 Me NMe₂ Br 2-128 Me O(CH₂)CONEt₂ Br 2-129 Me O(CH₂)-5-pyrrolidin- Br 2-one 2-130 Me SMe Br 2-131 Me SOMe Br 2-132 Me SO₂Me Br 2-133 Me SEt Br 2-134 Me SOEt Br 2-135 Me SO₂Et Br 2-136 Me SMe I 2-137 Me SOMe I 2-138 Me SO₂Me I 2-139 Me SEt I 2-140 Me SOEt I 2-141 Me SO₂Et I 2-142 Me Cl CF₃ 2-143 Me SMe CF₃ 2-144 Me SOMe CF₃ 2-145 Me SO₂Me CF₃ 2-146 Me SEt CF₃ 2-147 Me SOEt CF₃ 2-148 Me SO₂Et CF₃ 2-149 Me S(CH₂)₂OMe CF₃ 2-150 Me SO(CH₂)₂OMe CF₃ 2-151 Me SO₂(CH₂)₂OMe CF₃ 2-152 Me Me SO₂Me 2-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 2-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 2-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 2-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 2-157 Me NH₂ SO₂Me 2-158 Me NHMe SO₂Me 2-159 Me NMe₂ SO₂Me 2-160 Me NH(CH₂)₂OMe SO₂Me 2-161 Me pyrazol-1-yl SO₂Me 2-162 Me OH SO₂Me 2-163 Me OMe SO₂Me 2-164 Me OMe SO₂Et 2-165 Me OEt SO₂Me 2-166 Me OEt SO₂Et 2-167 Me OiPr SO₂Me 2-168 Me OiPr SO₂Et 2-169 Me O(CH₂)₂OMe SO₂Me 2-170 Me O(CH₂)₂OMe SO₂Et 2-171 Me O(CH₂)₃OMe SO₂Me 2-172 Me O(CH₂)₃OMe SO₂Et 2-173 Me O(CH₂)₄OMe SO₂Me 2-174 Me O(CH₂)₄OMe SO₂Et 2-175 Me O(CH₂)₂NHSO2Me SO₂Me 2-176 Me O(CH₂)₂NHSO2Me SO₂Et 2-177 Me OCH₂(CO)NMe₂ SO₂Me 2-178 Me OCH₂(CO)NMe₂ SO₂Et 2-179 Me [1,4]dioxan-2-yl- SO₂Me methoxy 2-180 Me [1,4]dioxan-2-yl- SO₂Et methoxy 2-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2- yl) 2-182 Me Cl SO₂Me 2-183 Me SMe SO₂Me 2-184 Me SOMe SO₂Me 2-185 Me SO₂Me SO₂Me 2-186 Me SO₂Me SO₂Et 2-187 Me SEt SO₂Me 2-188 Me SOEt SO₂Me 2-189 Me SO₂Et SO₂Me 2-190 Me S(CH₂)₂OMe SO₂Me 2-191 Me SO(CH₂)₂OMe SO₂Me 2-192 Me SO₂(CH₂)₂OMe SO₂Me 2-193 CH₂SMe OMe SO₂Me 2-194 CH₂OMe OMe SO₂Me 2-195 CH₂O(CH₂)₂ NH(CH₂)₂OEt SO₂Me OMe 2-196 CH₂O(CH₂)₂ NH(CH₂)₃OEt SO₂Me OMe 2-197 CH₂O(CH₂)₃ OMe SO₂Me OMe 2-198 CH₂O(CH₂)₂ NH(CH₂)₂OMe SO₂Me OMe 2-199 CH₂O(CH₂)₂ NH(CH₂)₃OMe SO₂Me OMe 2-200 Et SMe Cl 2-201 Et SO₂Me Cl 2-202 Et SMe CF₃ 2-203 Et SO₂Me CF₃ 2-204 Et F SO₂Me 2-205 Et NH(CH₂)₂OMe SO₂Me 2-206 iPr SO₂Me CF₃ 2-207 cPr SO₂Me CF₃ 2-208 CF₃ O(CH₂)₂OMe F 2-209 CF₃ O(CH₂)₃OMe F 2-210 CF₃ OCH₂CONMe₂ F 2-211 CF₃ [1,4]dioxan-2-yl- F methoxy 2-212 CF₃ O(CH₂)₂OMe Cl 2-213 CF₃ O(CH₂)₃OMe Cl 2-214 CF₃ OCH₂CONMe₂ Cl 2-215 CF₃ [1,4]dioxan-2-yl- Cl methoxy 2-216 CF₃ O(CH₂)₂OMe Br 2-217 CF₃ O(CH₂)₃OMe Br 2-218 CF₃ OCH₂CONMe₂ Br 2-219 CF₃ [1,4]dioxan-2-yl- Br methoxy 2-220 CF₃ O(CH₂)₂OMe I 2-221 CF₃ O(CH₂)₃OMe I 2-222 CF₃ OCH₂CONMe₂ I 2-223 CF₃ [1,4]dioxan-2-yl- I methoxy 2-224 CF₃ F SO₂Me 2-225 CF₃ F SO₂Et 2-226 CF₃ O(CH₂)₂OMe SO₂Me 2-227 CF₃ O(CH₂)₂OMe SO₂Et 2-228 CF₃ O(CH₂)₃OMe SO₂Me 2-229 CF₃ O(CH₂)₃OMe SO₂Et 2-230 CF₃ OCH₂CONMe₂ SO₂Me 2-231 CF₃ OCH₂CONMe₂ SO₂Et 2-232 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 2-233 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 2-234 F SMe CF₃ 2-235 F SOMe CF₃ 2-236 Cl Me Cl 2-237 Cl OCH₂CHCH₂ Cl 2-238 Cl OCH₂CHF₂ Cl 2-239 Cl O(CH₂)₂OMe Cl 2-240 Cl OCH₂(CO)NMe₂ Cl 2-241 Cl O(CH₂)-5-pyrrolidin- Cl 2-one 2-242 Cl SMe Cl 2-243 Cl SOMe Cl 2-244 Cl SO₂Me Cl 2-245 Cl F SMe 2-246 Cl Cl SO₂Me 2-247 Cl COOMe SO₂Me 2-248 Cl CONMe₂ SO₂Me 2-249 Cl CONMe(OMe) SO₂Me 2-250 Cl CH₂OMe SO₂Me 2-251 Cl CH₂OMe SO₂Et 2-252 Cl CH₂OEt SO₂Me 2-253 Cl CH₂OEt SO₂Et 2-254 Cl CH₂OCH₂CHF₂ SO₂Me 2-255 Cl CH₂OCH₂CF₃ SO₂Me 2-256 Cl CH₂OCH₂CF₃ SO₂Et 2-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 2-258 Cl CH₂OcPentyl SO₂Me 2-259 Cl CH₂PO(OMe)₂ SO₂Me 2-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 2-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 2-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 2-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 2-264 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 2-265 Cl 5-(methoxymethyl)- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 2-266 Cl 5-(methoxymethyl)- SO₂Et 5-methyl-4,5- dihydro-1,2-oxazol- 3-yl 2-267 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 2-268 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 2-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 2-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 2-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 2-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 2-273 Cl OMe SO₂Me 2-274 Cl OMe SO₂Et 2-275 Cl OEt SO₂Me 2-276 Cl OEt SO₂Et 2-277 Cl OiPr SO₂Me 2-278 Cl OiPr SO₂Et 2-279 Cl O(CH₂)₂OMe SO₂Me 2-280 Cl O(CH₂)₄OMe SO₂Me 2-281 Cl O(CH₂)₄OMe SO₂Et 2-282 Cl O(CH₂)₃OMe SO₂Me 2-283 Cl O(CH₂)₃OMe SO₂Et 2-284 Cl O(CH₂)₂OMe SO₂Me 2-285 Cl O(CH₂)₂OMe SO₂Et 2-286 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 2-287 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 2-288 Cl OCH₂(CO)NMe₂ SO₂Me 2-289 Cl OCH₂(CO)NMe₂ SO₂Et 2-290 Cl SMe SO₂Me 2-291 Cl SOMe SO₂Me 2-292 Br OMe Br 2-293 Br O(CH₂)₂OMe Br 2-294 Br O(CH₂)₂OMe SO₂Me 2-295 Br O(CH₂)₂OMe SO₂Et 2-296 Br O(CH₂)₃OMe SO₂Me 2-297 Br O(CH₂)₃OMe SO₂Et 2-298 Br O(CH₂)₄OMe SO₂Me 2-299 Br O(CH₂)₄OMe SO₂Et 2-300 Br [1,4]dioxan-2-yl- SO₂Me methoxy 2-301 Br [1,4]dioxan-2-yl- SO₂Et methoxy 2-302 I O(CH₂)₂OMe SO₂Me 2-303 I O(CH₂)₂OMe SO₂Et 2-304 I O(CH₂)₃OMe SO₂Me 2-305 I O(CH₂)₃OMe SO₂Et 2-306 I O(CH₂)₄OMe SO₂Me 2-307 I O(CH₂)₄OMe SO₂Et 2-308 I [1,4]dioxan-2-yl- SO₂Me methoxy 2-309 I [1,4]dioxan-2-yl- SO₂Et methoxy 2-310 OMe SMe CF₃ 2-311 OMe SOMe CF₃ 2-312 OMe SO₂Me CF₃ 2-313 OMe SOEt CF₃ 2-314 OMe SO₂Et CF₃ 2-315 OMe S(CH₂)₂OMe CF₃ 2-316 OMe SO(CH₂)₂OMe CF₃ 2-317 OMe SO₂(CH₂)₂OMe CF₃ 2-318 OMe SMe Cl 2-319 OMe SOMe Cl 2-320 OMe SO₂Me Cl 2-321 OMe SEt Cl 2-322 OMe SOEt Cl 2-323 OMe SO₂Et Cl 2-324 OMe S(CH₂)₂OMe Cl 2-325 OMe SO(CH₂)₂OMe Cl 2-326 OMe SO₂(CH₂)₂OMe Cl 2-327 OCH₂c-Pr SMe CF₃ 2-328 OCH₂c-Pr SOMe CF₃ 2-329 OCH₂c-Pr SO₂Me CF₃ 2-330 OCH₂c-Pr SEt CF₃ 2-331 OCH₂c-Pr SOEt CF₃ 2-332 OCH₂c-Pr SO₂Et CF₃ 2-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 2-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 2-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 2-336 OCH₂c-Pr SMe Cl 2-337 OCH₂c-Pr SOMe Cl 2-338 OCH₂c-Pr SO₂Me Cl 2-339 OCH₂c-Pr SEt Cl 2-340 OCH₂c-Pr SOEt Cl 2-341 OCH₂c-Pr SO₂Et Cl 2-342 OCH₂c-Pr S(CH₂)₂OMe Cl 2-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 2-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 2-345 OCH₂c-Pr SMe SO₂Me 2-346 OCH₂c-Pr SOMe SO₂Me 2-347 OCH₂c-Pr SO₂Me SO₂Me 2-348 OCH₂c-Pr SEt SO₂Me 2-349 OCH₂c-Pr SOEt SO₂Me 2-350 OCH₂c-Pr SO₂Et SO₂Me 2-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 2-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 2-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 2-354 SO₂Me F CF₃ 2-355 SO₂Me NH₂ CF₃ 2-356 SO₂Me NHEt Cl 2-357 SMe SEt F 2-358 SMe SMe F 2-359 Cl SMe CF₃ 2-360 Cl S(O)Me CF₃ 2-361 Cl SO₂Me CF₃ 2-362 Cl SO₂Me SO₂Me 2-363 Cl 1H-pyrazol-1-yl CF₃ 2-364 Cl O(CH₂)₂F CF₃

TABLE 3 Compounds of the general formula (I) in which A is CY and R is ethyl, and X, Y, and Z are as defined below.

No. X Y Z 3-1  F H Cl 3-2  F H SO₂Me 3-3  F H SO₂Et 3-4  F H CF₃ 3-5  F H NO₂ 3-6  Cl H Br 3-7  Cl H SMe 3-8  Cl H SOMe 3-9  Cl H SO₂Me 3-10  Cl H SO₂CH₂Cl 3-11  Cl H SEt 3-12  Cl H SO₂Et 3-13  Cl H CF₃ 3-14  Cl H NO₂ 3-15  Cl H pyrazol-1-yl 3-16  Cl H 1H-1,2,4- triazol-1-yl 3-17  Br H Cl 3-18  Br H Br 3-19  Br H SO₂Me 3-20  Br H SO₂Et 3-21  Br H CF₃ 3-22  SO₂Me H Cl 3-23  SO₂Me H Br 3-24  SO₂Me H SMe 3-25  SO₂Me H SOMe 3-26  SO₂Me H SO₂Me 3-27  SO₂Me H SO₂Et 3-28  SO₂Me H CF₃ 3-29  SO₂Et H Cl 3-30  SO₂Et H Br 3-31  SO₂Et H SMe 3-32  SO₂Et H SOMe 3-33  SO₂Et H SO₂Me 3-34  SO₂Et H CF₃ 3-35  NO₂ H F 3-36  NO₂ H Cl 3-37  NO₂ H Br 3-38  NO₂ H I 3-39  NO₂ H CN 3-40  NO₂ H SO₂Me 3-41  NO₂ H SO₂Et 3-42  NO₂ H CF₃ 3-43  Me H Cl 3-44  Me H Br 3-45  Me H SMe 3-46  Me H SO₂Me 3-47  Me H SO₂CH₂Cl 3-48  Me H SEt 3-49  Me H SO₂Et 3-50  Me H CF₃ 3-51  CH₂SO₂Me H CF₃ 3-52  Et H Cl 3-53  Et H Br 3-54  Et H SMe 3-55  Et H SO₂Me 3-56  Et H SO₂CH₂Cl 3-57  Et H SEt 3-58  Et H SO₂Et 3-59  Et H CF₃ 3-60  CF₃ H Cl 3-61  CF₃ H Br 3-62  CF₃ H SO₂Me 3-63  CF₃ H SO₂Et 3-64  CF₃ H CF₃ 3-65  NO₂ NH₂ F 3-66  NO₂ NHMe F 3-67  NO₂ NMe₂ F 3-68  NO₂ Me Cl 3-69  NO₂ NH₂ Cl 3-70  NO₂ NHMe Cl 3-71  NO₂ NMe₂ Cl 3-72  NO₂ NH₂ Br 3-73  NO₂ NHMe Br 3-74  NO₂ NMe₂ Br 3-75  NO₂ NH₂ CF₃ 3-76  NO₂ NMe₂ CF₃ 3-77  NO₂ NH₂ SO₂Me 3-78  NO₂ NH₂ SO₂Et 3-79  NO₂ NHMe SO₂Me 3-80  NO₂ NMe₂ SO₂Me 3-81  NO₂ NMe₂ SO₂Et 3-82  NO₂ NH₂ 1H-1,2,4- triazol-1-yl 3-83  NO₂ NHMe 1H-1,2,4- triazol-1-yl 3-84  NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 3-85  Me SMe H 3-86  Me SOMe H 3-87  Me SO₂Me H 3-88  Me SEt H 3-89  Me SOEt H 3-90  Me SO₂Et H 3-91  Me S(CH₂)₂OMe H 3-92  Me SO(CH₂)₂OMe H 3-93  Me SO₂(CH₂)₂OMe H 3-94  Me F F 3-95  Me F Cl 3-96  Me SEt F 3-97  Me SOEt F 3-98  Me SO₂Et F 3-99  Me Me Cl 3-100 Me F Cl 3-101 Me Cl Cl 3-102 Me NH₂ Cl 3-103 Me NHMe Cl 3-104 Me NMe₂ Cl 3-105 Me O(CH₂)₂OMe Cl 3-106 Me O(CH₂)₃OMe Cl 3-107 Me O(CH₂)₄OMe Cl 3-108 Me OCH₂CONMe₂ Cl 3-109 Me O(CH₂)₂—CONMe₂ Cl 3-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 3-111 Me O(CH₂)₂—NHCO₂Et Cl 3-112 Me O(CH₂)₂NHCO₂Me Cl 3-113 Me OCH₂NHSO₂cPr Cl 3-114 Me O(CH₂)-5-2,4-di- Cl methyl-2,4-dihydro- 3H-1,2,4-triazol-3- one 3-115 Me O(CH₂)-3,5- Cl dimethyl-1,2-oxazol- 4-yl 3-116 Me SMe Cl 3-117 Me SOMe Cl 3-118 Me SO₂Me Cl 3-119 Me SEt Cl 3-120 Me SOEt Cl 3-121 Me SO₂Et Cl 3-122 Me S(CH₂)₂OMe Cl 3-123 Me SO(CH₂)₂OMe Cl 3-124 Me SO₂(CH₂)₂OMe Cl 3-125 Me NH₂ Br 3-126 Me NHMe Br 3-127 Me NMe₂ Br 3-128 Me OCH₂CONMe₂ Br 3-129 Me O(CH₂)-5-pyrrolidin- Br 2-one 3-130 Me SMe Br 3-131 Me SOMe Br 3-132 Me SO₂Me Br 3-133 Me SEt Br 3-134 Me SOEt Br 3-135 Me SO₂Et Br 3-136 Me SMe I 3-137 Me SOMe I 3-138 Me SO₂Me I 3-139 Me SEt I 3-140 Me SOEt I 3-141 Me SO₂Et I 3-142 Me Cl CF₃ 3-143 Me SMe CF₃ 3-144 Me SOMe CF₃ 3-145 Me SO₂Me CF₃ 3-146 Me SEt CF₃ 3-147 Me SOEt CF₃ 3-148 Me SO₂Et CF₃ 3-149 Me S(CH₂)₂OMe CF₃ 3-150 Me SO(CH₂)₂OMe CF₃ 3-151 Me SO₂(CH₂)₂OMe CF₃ 3-152 Me Me SO₂Me 3-153 Me 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 3-154 Me 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 3-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 3-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 3-157 Me NH₂ SO₂Me 3-158 Me NHMe SO₂Me 3-159 Me NMe₂ SO₂Me 3-160 Me NH(CH₂)₂OMe SO₂Me 3-161 Me pyrazol-1-yl SO₂Me 3-162 Me OH SO₂Me 3-163 Me OMe SO₂Me 3-164 Me OMe SO₂Et 3-165 Me OEt SO₂Me 3-166 Me OEt SO₂Et 3-167 Me OiPr SO₂Me 3-168 Me OiPr SO₂Et 3-169 Me O(CH₂)₂OMe SO₂Me 3-170 Me O(CH₂)₂OMe SO₂Et 3-171 Me O(CH₂)₃OMe SO₂Me 3-172 Me O(CH₂)₃OMe SO₂Et 3-173 Me O(CH₂)₄OMe SO₂Me 3-174 Me O(CH₂)₄OMe SO₂Et 3-175 Me O(CH₂)₂NHSO2Me SO₂Me 3-176 Me O(CH₂)₂NHSO2Me SO₂Et 3-177 Me OCH₂(CO)NMe₂ SO₂Me 3-178 Me OCH₂(CO)NMe₂ SO₂Et 3-179 Me [1,4]dioxan-2-yl- SO₂Me methoxy 3-180 Me [1,4]dioxan-2-yl- SO₂Et methoxy 3-181 Me O(CH₂)₂—O-(3,5- SO₂Me dimethoxypyrimidin- 2-yl) 3-182 Me Cl SO₂Me 3-183 Me SMe SO₂Me 3-184 Me SOMe SO₂Me 3-185 Me SO₂Me SO₂Me 3-186 Me SO₂Me SO₂Et 3-187 Me SEt SO₂Me 3-188 Me SOEt SO₂Me 3-189 Me SO₂Et SO₂Me 3-190 Me S(CH₂)₂OMe SO₂Me 3-191 Me SO(CH₂)₂OMe SO₂Me 3-192 Me SO₂(CH₂)₂OMe SO₂Me 3-193 CH₂SMe OMe SO₂Me 3-194 CH₂OMe OMe SO₂Me 3-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 3-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 3-197 CH₂O(CH₂)₃OMe OMe SO₂Me 3-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 3-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 3-200 Et SMe Cl 3-201 Et SO₂Me Cl 3-202 Et SMe CF₃ 3-203 Et SO₂Me CF₃ 3-204 Et F SO₂Me 3-205 Et NH(CH₂)₂OMe SO₂Me 3-206 iPr SO₂Me CF₃ 3-207 cPr SO₂Me CF₃ 3-208 CF₃ O(CH₂)₂OMe F 3-209 CF₃ O(CH₂)₃OMe F 3-210 CF₃ OCH₂CONMe₂ F 3-211 CF₃ [1,4]dioxan-2-yl- F methoxy 3-212 CF₃ O(CH₂)₂OMe Cl 3-213 CF₃ O(CH₂)₃OMe Cl 3-214 CF₃ OCH₂CONMe₂ Cl 3-215 CF₃ [1,4]dioxan-2-yl- Cl methoxy 3-216 CF₃ O(CH₂)₂OMe Br 3-217 CF₃ O(CH₂)₃OMe Br 3-218 CF₃ OCH₂CONMe₂ Br 3-219 CF₃ [1,4]dioxan-2-yl- Br methoxy 3-220 CF₃ O(CH₂)₂OMe I 3-221 CF₃ O(CH₂)₃OMe I 3-222 CF₃ OCH₂CONMe₂ I 3-223 CF₃ [1,4]dioxan-2-yl- I methoxy 3-224 CF₃ F SO₂Me 3-225 CF₃ F SO₂Et 3-226 CF₃ O(CH₂)₂OMe SO₂Me 3-227 CF₃ O(CH₂)₂OMe SO₂Et 3-228 CF₃ O(CH₂)₃OMe SO₂Me 3-229 CF₃ O(CH₂)₃OMe SO₂Et 3-230 CF₃ OCH₂CONMe₂ SO₂Me 3-231 CF₃ OCH₂CONMe₂ SO₂Et 3-232 CF₃ [1,4]dioxan-2-yl- SO₂Me methoxy 3-233 CF₃ [1,4]dioxan-2-yl- SO₂Et methoxy 3-234 F SMe CF₃ 3-235 F SOMe CF₃ 3-236 Cl Me Cl 3-237 Cl OCH₂CHCH₂ Cl 3-238 Cl OCH₂CHF₂ Cl 3-239 Cl O(CH₂)₂OMe Cl 3-240 Cl OCH₂(CO)NMe₂ Cl 3-241 Cl O(CH₂)-5- Cl pyrrolidin-2-one 3-242 Cl SMe Cl 3-243 Cl SOMe Cl 3-244 Cl SO₂Me Cl 3-245 Cl F SMe 3-246 Cl Cl SO₂Me 3-247 Cl COOMe SO₂Me 3-248 Cl CONMe₂ SO₂Me 3-249 Cl CONMe(OMe) SO₂Me 3-250 Cl CH₂OMe SO₂Me 3-251 Cl CH₂OMe SO₂Et 3-252 Cl CH₂OEt SO₂Me 3-253 Cl CH₂OEt SO₂Et 3-254 Cl CH₂OCH₂CHF₂ SO₂Me 3-255 Cl CH₂OCH₂CF₃ SO₂Me 3-256 Cl CH₂OCH₂CF₃ SO₂Et 3-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 3-258 Cl CH₂OcPentyl SO₂Me 3-259 Cl CH₂PO(OMe)₂ SO₂Me 3-260 Cl 4,5-dihydro-1,2- SMe oxazol-3-yl 3-261 Cl 4,5-dihydro-1,2- SO₂Me oxazol-3-yl 3-262 Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 3-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol- 3-yl 3-264 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 3-265 Cl 5-(methoxymethyl)- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 3-266 Cl 5-(methoxymethyl)- SO₂Et 5-methyl-4,5-dihydro- 1,2-oxazol-3-yl 3-267 Cl CH₂O- SO₂Me tetrahydrofuran-3-yl 3-268 Cl CH₂O- SO₂Et tetrahydrofuran-3-yl 3-269 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 3-270 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-2-yl 3-271 Cl CH₂OCH₂- SO₂Me tetrahydrofuran-3-yl 3-272 Cl CH₂OCH₂- SO₂Et tetrahydrofuran-3-yl 3-273 Cl OMe SO₂Me 3-274 Cl OMe SO₂Et 3-275 Cl OEt SO₂Me 3-276 Cl OEt SO₂Et 3-277 Cl OiPr SO₂Me 3-278 Cl OiPr SO₂Et 3-279 Cl O(CH₂)₂OMe SO₂Me 3-280 Cl O(CH₂)₄OMe SO₂Me 3-281 Cl O(CH₂)₄OMe SO₂Et 3-282 Cl O(CH₂)₃OMe SO₂Me 3-283 Cl O(CH₂)₃OMe SO₂Et 3-284 Cl O(CH₂)₂OMe SO₂Me 3-285 Cl O(CH₂)₂OMe SO₂Et 3-286 Cl [1,4]dioxan-2-yl- SO₂Me methoxy 3-287 Cl [1,4]dioxan-2-yl- SO₂Et methoxy 3-288 Cl OCH₂(CO)NMe₂ SO₂Me 3-289 Cl OCH₂(CO)NMe₂ SO₂Et 3-290 Cl SMe SO₂Me 3-291 Cl SOMe SO₂Me 3-292 Br OMe Br 3-293 Br O(CH₂)₂OMe Br 3-294 Br O(CH₂)₂OMe SO₂Me 3-295 Br O(CH₂)₂OMe SO₂Et 3-296 Br O(CH₂)₃OMe SO₂Me 3-297 Br O(CH₂)₃OMe SO₂Et 3-298 Br O(CH₂)₄OMe SO₂Me 3-299 Br O(CH₂)₄OMe SO₂Et 3-300 Br [1,4]dioxan-2-yl- SO₂Me methoxy 3-301 Br [1,4]dioxan-2-yl- SO₂Et methoxy 3-302 I O(CH₂)₂OMe SO₂Me 3-303 I O(CH₂)₂OMe SO₂Et 3-304 I O(CH₂)₃OMe SO₂Me 3-305 I O(CH₂)₃OMe SO₂Et 3-306 I O(CH₂)₄OMe SO₂Me 3-307 I O(CH₂)₄OMe SO₂Et 3-308 I [1,4]dioxan-2-yl- SO₂Me methoxy 3-309 I [1,4]dioxan-2-yl- SO₂Et methoxy 3-310 OMe SMe CF₃ 3-311 OMe SOMe CF₃ 3-312 OMe SO₂Me CF₃ 3-313 OMe SOEt CF₃ 3-314 OMe SO₂Et CF₃ 3-315 OMe S(CH₂)₂OMe CF₃ 3-316 OMe SO(CH₂)₂OMe CF₃ 3-317 OMe SO₂(CH₂)₂OMe CF₃ 3-318 OMe SMe Cl 3-319 OMe SOMe Cl 3-320 OMe SO₂Me Cl 3-321 OMe SEt Cl 3-322 OMe SOEt Cl 3-323 OMe SO2Et Cl 3-324 OMe S(CH₂)₂OMe Cl 3-325 OMe SO(CH₂)₂OMe Cl 3-326 OMe SO₂(CH₂)₂OMe Cl 3-327 OCH₂c-Pr SMe CF₃ 3-328 OCH₂c-Pr SOMe CF₃ 3-329 OCH₂c-Pr SO₂Me CF₃ 3-330 OCH₂c-Pr SEt CF₃ 3-331 OCH₂c-Pr SOEt CF₃ 3-332 OCH₂c-Pr SO₂Et CF₃ 3-333 OCH₂c-Pr S(CH₂)₂OMe CF₃ 3-334 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 3-335 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 3-336 OCH₂c-Pr SMe Cl 3-337 OCH₂c-Pr SOMe Cl 3-338 OCH₂c-Pr SO₂Me Cl 3-339 OCH₂c-Pr SEt Cl 3-340 OCH₂c-Pr SOEt Cl 3-341 OCH₂c-Pr SO₂Et Cl 3-342 OCH₂c-Pr S(CH₂)₂OMe Cl 3-343 OCH₂c-Pr SO(CH₂)₂OMe Cl 3-344 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 3-345 OCH₂c-Pr SMe SO₂Me 3-346 OCH₂c-Pr SOMe SO₂Me 3-347 OCH₂c-Pr SO₂Me SO₂Me 3-348 OCH₂c-Pr SEt SO₂Me 3-349 OCH₂c-Pr SOEt SO₂Me 3-350 OCH₂c-Pr SO₂Et SO₂Me 3-351 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 3-352 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 3-353 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 3-354 SO₂Me F CF₃ 3-355 SO₂Me NH₂ CF₃ 3-356 SO₂Me NHEt Cl 3-357 SMe SEt F 3-358 SMe SMe F 3-359 Cl SMe CF₃ 3-360 Cl S(O)Me CF₃ 3-361 Cl SO₂Me CF₃ 3-362 Cl SO₂Me SO₂Me

TABLE 4 Compound of the general formula (I) in which A is CY and R is trifluoromethyl, and X, Y, and Z are as defined below.

No. X Y Z 4-1  F H Cl 4-2  F H SO₂Me 4-3  F H SO₂Et 4-4  F H CF₃ 4-5  F H NO₂ 4-6  Cl H Br 4-7  Cl H SMe 4-8  Cl H SOMe 4-9  Cl H SO₂Me 4-10  Cl H SO₂CH₂Cl 4-11  Cl H SEt 4-12  Cl H SO₂Et 4-13  Cl H CF₃ 4-14  Cl H NO₂ 4-15  Cl H pyrazol-1-yl 4-16  Cl H 1H-1,2,4- triazol-1-yl 4-17  Br H Cl 4-18  Br H Br 4-19  Br H SO₂Me 4-20  Br H SO₂Et 4-21  Br H CF₃ 4-22  SO₂Me H Cl 4-23  SO₂Me H Br 4-24  SO₂Me H SMe 4-25  SO₂Me H SOMe 4-26  SO₂Me H SO₂Me 4-27  SO₂Me H SO₂Et 4-28  SO₂Me H CF₃ 4-29  SO₂Et H Cl 4-30  SO₂Et H Br 4-31  SO₂Et H SMe 4-32  SO₂Et H SOMe 4-33  SO₂Et H SO₂Me 4-34  SO₂Et H CF₃ 4-35  NO₂ H F 4-36  NO₂ H Cl 4-37  NO₂ H Br 4-38  NO₂ H I 4-39  NO₂ H CN 4-40  NO₂ H SO₂Me 4-41  NO₂ H SO₂Et 4-42  NO₂ H CF₃ 4-43  Me H Cl 4-44  Me H Br 4-45  Me H SMe 4-46  Me H SO₂Me 4-47  Me H SO₂CH₂Cl 4-48  Me H SEt 4-49  Me H SO₂Et 4-50  Me H CF₃ 4-51  CH₂SO₂Me H CF₃ 4-52  Et H Cl 4-53  Et H Br 4-54  Et H SMe 4-55  Et H SO₂Me 4-56  Et H SO₂CH₂Cl 4-57  Et H SEt 4-58  Et H SO₂Et 4-59  Et H CF₃ 4-60  CF₃ H Cl 4-61  CF₃ H Br 4-62  CF₃ H SO₂Me 4-63  CF₃ H SO₂Et 4-64  CF₃ H CF₃ 4-65  NO₂ NH₂ F 4-66  NO₂ NHMe F 4-67  NO₂ NMe₂ F 4-68  NO₂ Me Cl 4-69  NO₂ NH₂ Cl 4-70  NO₂ NHMe Cl 4-71  NO₂ NMe₂ Cl 4-72  NO₂ NH₂ Br 4-73  NO₂ NHMe Br 4-74  NO₂ NMe₂ Br 4-75  NO₂ NH₂ CF₃ 4-76  NO₂ NMe₂ CF₃ 4-77  NO₂ NH₂ SO₂Me 4-78  NO₂ NH₂ SO₂Et 4-79  NO₂ NHMe SO₂Me 4-80  NO₂ NMe₂ SO₂Me 4-81  NO₂ NMe₂ SO₂Et 4-82  NO₂ NH₂ 1H-1,2,4- triazol-1-yl 4-83  NO₂ NHMe 1H-1,2,4- triazol-1-yl 4-84  NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 4-85  Me SMe H 4-86  Me SOMe H 4-87  Me SO₂Me H 4-88  Me SEt H 4-89  Me SOEt H 4-90  Me SO₂Et H 4-91  Me S(CH₂)₂OMe H 4-92  Me SO(CH₂)₂OMe H 4-93  Me SO₂(CH₂)₂OMe H 4-94  Me F F 4-95  Me F Cl 4-96  Me SEt F 4-97  Me SOEt F 4-98  Me SO₂Et F 4-99  Me Me Cl 4-100 Me F Cl 4-101 Me Cl Cl 4-102 Me NH₂ Cl 4-103 Me NHMe Cl 4-104 Me NMe₂ Cl 4-105 Me O(CH₂)₂OMe Cl 4-106 Me O(CH₂)₃OMe Cl 4-107 Me O(CH₂)₄OMe Cl 4-108 Me OCH₂CONMe₂ Cl 4-109 Me O(CH₂)₂—CO—NMe₂ Cl 4-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 4-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 4-112 Me O(CH₂)₂—NHCO₂Me Cl 4-113 Me OCH₂—NHSO₂cPr Cl 4-114 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 4-115 Me O(CH₂)-3,5-dimethyl- Cl 1,2-oxazol-4-yl 4-116 Me SMe Cl 4-117 Me SOMe Cl 4-118 Me SO₂Me Cl 4-119 Me SEt Cl 4-120 Me SOEt Cl 4-121 Me SO₂Et Cl 4-122 Me S(CH₂)₂OMe Cl 4-123 Me SO(CH₂)₂OMe Cl 4-124 Me SO₂(CH₂)₂OMe Cl 4-125 Me NH₂ Br 4-126 Me NHMe Br 4-127 Me NMe₂ Br 4-128 Me OCH₂(CO)NMe₂ Br 4-129 Me O(CH₂)-5-pyrrolidin-2-one Br 4-130 Me SMe Br 4-131 Me SOMe Br 4-132 Me SO₂Me Br 4-133 Me SEt Br 4-134 Me SOEt Br 4-135 Me SO₂Et Br 4-136 Me SMe I 4-137 Me SOMe I 4-138 Me SO₂Me I 4-139 Me SEt I 4-140 Me SOEt I 4-141 Me SO₂Et I 4-142 Me Cl CF₃ 4-143 Me SMe CF₃ 4-144 Me SOMe CF₃ 4-145 Me SO₂Me CF₃ 4-146 Me SEt CF₃ 4-147 Me SOEt CF₃ 4-148 Me SO₂Et CF₃ 4-149 Me S(CH₂)₂OMe CF₃ 4-150 Me SO(CH₂)₂OMe CF₃ 4-151 Me SO₂(CH₂)₂OMe CF₃ 4-152 Me Me SO₂Me 4-153 Me 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 4-154 Me 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 4-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 4-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-157 Me NH₂ SO₂Me 4-158 Me NHMe SO₂Me 4-159 Me NMe₂ SO₂Me 4-160 Me NH(CH₂)₂OMe SO₂Me 4-161 Me pyrazol-1-yl SO₂Me 4-162 Me OH SO₂Me 4-163 Me OMe SO₂Me 4-164 Me OMe SO₂Et 4-165 Me OEt SO₂Me 4-166 Me OEt SO₂Et 4-167 Me OiPr SO₂Me 4-168 Me OiPr SO₂Et 4-169 Me O(CH₂)₂OMe SO₂Me 4-170 Me O(CH₂)₂OMe SO₂Et 4-171 Me O(CH₂)₃OMe SO₂Me 4-172 Me O(CH₂)₃OMe SO₂Et 4-173 Me O(CH₂)₄OMe SO₂Me 4-174 Me O(CH₂)₄OMe SO₂Et 4-175 Me O(CH₂)₂NHSO2Me SO₂Me 4-176 Me O(CH₂)₂NHSO2Me SO₂Et 4-177 Me OCH₂(CO)NMe₂ SO₂Me 4-178 Me OCH₂(CO)NMe₂ SO₂Et 4-179 Me [1,4]dioxan-2-yl-methoxy SO₂Me 4-180 Me [1,4]dioxan-2-yl-methoxy SO₂Et 4-181 Me O(CH₂)₂—O-(3,5-di- SO₂Me methoxypyrimidin-2-yl) 4-182 Me Cl SO₂Me 4-183 Me SMe SO₂Me 4-184 Me SOMe SO₂Me 4-185 Me SO₂Me SO₂Me 4-186 Me SO₂Me SO₂Et 4-187 Me SEt SO₂Me 4-188 Me SOEt SO₂Me 4-189 Me SO₂Et SO₂Me 4-190 Me S(CH₂)₂OMe SO₂Me 4-191 Me SO(CH₂)₂OMe SO₂Me 4-192 Me SO₂(CH₂)₂OMe SO2Me 4-193 CH₂SMe OMe SO₂Me 4-194 CH₂OMe OMe SO₂Me 4-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 4-196 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 4-197 CH₂O(CH₂)₂OMe OMe SO₂Me 4-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 4-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 4-200 Et SMe Cl 4-201 Et SO₂Me Cl 4-202 Et SMe CF₃ 4-203 Et SO₂Me CF₃ 4-204 Et F SO₂Me 4-205 Et NH(CH₂)₂OMe SO₂Me 4-206 iPr SO₂Me CF₃ 4-207 cPr SO₂Me CF₃ 4-208 CF₃ O(CH₂)₂OMe F 4-209 CF₃ O(CH₂)₃OMe F 4-210 CF₃ OCH₂CONMe₂ F 4-211 CF₃ [1,4]dioxan-2-yl-methoxy F 4-212 CF₃ O(CH₂)₂OMe Cl 4-213 CF₃ O(CH₂)₃OMe Cl 4-214 CF₃ OCH₂CONMe₂ Cl 4-215 CF₃ [1,4]dioxan-2-yl-methoxy Cl 4-216 CF₃ O(CH₂)₂OMe Br 4-217 CF₃ O(CH₂)₃OMe Br 4-218 CF₃ OCH₂CONMe₂ Br 4-219 CF₃ [1,4]dioxan-2-yl-methoxy Br 4-220 CF₃ O(CH₂)₂OMe I 4-221 CF₃ O(CH₂)₃OMe I 4-222 CF₃ OCH₂CONMe₂ I 4-223 CF₃ [1,4]dioxan-2-yl-methoxy I 4-224 CF₃ F SO₂Me 4-225 CF₃ F SO₂Et 4-226 CF₃ O(CH₂)₂OMe SO₂Me 4-227 CF₃ O(CH₂)₂OMe SO₂Et 4-228 CF₃ O(CH₂)₃OMe SO₂Me 4-229 CF₃ O(CH₂)₃OMe SO₂Et 4-230 CF₃ OCH₂CONMe₂ SO₂Me 4-231 CF₃ OCH₂CONMe₂ SO₂Et 4-232 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Me 4-233 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Et 4-234 F SMe CF₃ 4-235 F SOMe CF₃ 4-236 Cl Me Cl 4-237 Cl OCH₂CHCH₂ Cl 4-238 Cl OCH₂CHF₂ Cl 4-239 Cl O(CH₂)₂OMe Cl 4-240 Cl OCH₂CONMe₂ Cl 4-241 Cl O(CH₂)-5-pyrrolidin-2-one Cl 4-242 Cl SMe Cl 4-243 Cl SOMe Cl 4-244 Cl SO₂Me Cl 4-245 Cl F SMe 4-246 Cl Cl SO₂Me 4-247 Cl COOMe SO₂Me 4-248 Cl CONMe₂ SO₂Me 4-249 Cl CONMe(OMe) SO₂Me 4-250 Cl CH₂OMe SO₂Me 4-251 Cl CH₂OMe SO₂Et 4-252 Cl CH₂OEt SO₂Me 4-253 Cl CH₂OEt SO₂Et 4-254 Cl CH₂OCH₂CHF₂ SO₂Me 4-255 Cl CH₂OCH₂CF₃ SO₂Me 4-256 Cl CH₂OCH₂CF₃ SMe 4-257 Cl CH₂OCH₂CF₃ SO₂Et 4-258 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 4-259 Cl CH₂OcPentyl SO₂Me 4-260 Cl CH₂PO(OMe)₂ SO₂Me 4-261 Cl 4,5-dihydro-1,2-oxazol-3-yl SMe 4-262 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 4-263 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 4-264 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 4-265 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-266 Cl 5-(methoxymethyl)-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 4-267 Cl 5-(methoxymethyl)-5- SO₂Et methyl-4,5-dihydro- 1,2-oxazol-3-yl 4-268 Cl CH₂O-tetrahydrofuran-3-yl SO₂Me 4-269 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et 4-270 Cl CH₂OCH₂-tetrahydrofuran- SO₂Me 2-yl 4-271 Cl CH₂OCH₂-tetrahydrofuran- SO₂Et 2-yl 4-272 Cl CH₂OCH₂-tetrahydrofuran- SO₂Me 3-yl 4-273 Cl CH₂OCH₂-tetrahydrofuran- SO₂Et 3-yl 4-274 Cl OMe SO₂Me 4-275 Cl OMe SO₂Et 4-276 Cl OEt SO₂Me 4-277 Cl OEt SO₂Et 4-278 Cl OiPr SO₂Me 4-279 Cl OiPr SO₂Et 4-280 Cl O(CH₂)₂OMe SO₂Me 4-281 Cl O(CH₂)₄OMe SO₂Me 4-282 Cl O(CH₂)₄OMe SO₂Et 4-283 Cl O(CH₂)₃OMe SO₂Me 4-284 Cl O(CH₂)₃OMe SO₂Et 4-285 Cl O(CH₂)₂OMe SO₂Me 4-286 Cl O(CH₂)₂OMe SO₂Et 4-287 Cl [1,4]dioxan-2-yl-methoxy SO₂Me 4-288 Cl [1,4]dioxan-2-yl-methoxy SO₂Et 4-289 Cl OCH₂(CO)NMe₂ SO₂Me 4-290 Cl OCH₂(CO)NMe₂ SO₂Et 4-291 Cl SMe SO₂Me 4-292 Cl SOMe SO₂Me 4-293 Br OMe Br 4-294 Br O(CH₂)₂OMe Br 4-295 Br O(CH₂)₂OMe SO₂Me 4-296 Br O(CH₂)₂OMe SO₂Et 4-297 Br O(CH₂)₃OMe SO₂Me 4-298 Br O(CH₂)₃OMe SO₂Et 4-299 Br O(CH₂)₄OMe SO₂Me 4-300 Br O(CH₂)₄OMe SO₂Et 4-301 Br [1,4]dioxan-2-yl-methoxy SO₂Me 4-302 Br [1,4]dioxan-2-yl-methoxy SO₂Et 4-303 I O(CH₂)₂OMe SO₂Me 4-304 I O(CH₂)₂OMe SO₂Et 4-305 I O(CH₂)₃OMe SO₂Me 4-306 I O(CH₂)₃OMe SO₂Et 4-307 I O(CH₂)₄OMe SO₂Me 4-308 I O(CH₂)₄OMe SO₂Et 4-309 I [1,4]dioxan-2-yl-methoxy SO₂Me 4-310 I [1,4]dioxan-2-yl-methoxy SO₂Et 4-311 OMe SMe CF₃ 4-312 OMe SOMe CF₃ 4-313 OMe SO₂Me CF₃ 4-314 OMe SOEt CF₃ 4-315 OMe SO₂Et CF₃ 4-316 OMe S(CH₂)₂OMe CF₃ 4-317 OMe SO(CH₂)₂OMe CF₃ 4-318 OMe SO₂(CH₂)₂OMe CF₃ 4-319 OMe SMe Cl 4-320 OMe SOMe Cl 4-321 OMe SO₂Me Cl 4-322 OMe SEt Cl 4-323 OMe SOEt Cl 4-324 OMe SO2Et Cl 4-325 OMe S(CH₂)₂OMe Cl 4-326 OMe SO(CH₂)₂OMe Cl 4-327 OMe SO₂(CH₂)₂OMe Cl 4-328 OCH₂c-Pr SMe CF₃ 4-329 OCH₂c-Pr SOMe CF₃ 4-330 OCH₂c-Pr SO₂Me CF₃ 4-331 OCH₂c-Pr SEt CF₃ 4-332 OCH₂c-Pr SOEt CF₃ 4-333 OCH₂c-Pr SO₂Et CF₃ 4-334 OCH₂c-Pr S(CH₂)₂OMe CF₃ 4-335 OCH₂c-Pr SO(CH₂)₂OMe CF₃ 4-336 OCH₂c-Pr SO₂(CH₂)₂OMe CF₃ 4-337 OCH₂c-Pr SMe Cl 4-338 OCH₂c-Pr SOMe Cl 4-339 OCH₂c-Pr SO₂Me Cl 4-340 OCH₂c-Pr SEt Cl 4-341 OCH₂c-Pr SOEt Cl 4-342 OCH₂c-Pr SO₂Et Cl 4-343 OCH₂c-Pr S(CH₂)₂OMe Cl 4-344 OCH₂c-Pr SO(CH₂)₂OMe Cl 4-345 OCH₂c-Pr SO₂(CH₂)₂OMe Cl 4-346 OCH₂c-Pr SMe SO₂Me 4-347 OCH₂c-Pr SOMe SO₂Me 4-348 OCH₂c-Pr SO₂Me SO₂Me 4-349 OCH₂c-Pr SEt SO₂Me 4-350 OCH₂c-Pr SOEt SO₂Me 4-351 OCH₂c-Pr SO₂Et SO₂Me 4-352 OCH₂c-Pr S(CH₂)₂OMe SO₂Me 4-353 OCH₂c-Pr SO(CH₂)₂OMe SO₂Me 4-354 OCH₂c-Pr SO₂(CH₂)₂OMe SO₂Me 4-355 SO₂Me F CF₃ 4-356 SO₂Me NH₂ CF₃ 4-357 SO₂Me NHEt Cl 4-358 SMe SEt F 4-359 SMe SMe F 4-360 Cl SMe CF₃ 4-361 Cl S(O)Me CF₃ 4-362 Cl SO₂Me CF₃ 4-363 Cl SO₂Me SO₂Me

TABLE 5 Compounds of the general formula (I) in which A is CY and R is CH₂OMe, and X, Y, and Z are as defined below.

No. X Y Z 5-1  F H Cl 5-2  F H SO₂Me 5-3  F H SO₂Et 5-4  F H CF₃ 5-5  F H NO₂ 5-6  Cl H Br 5-7  Cl H SMe 5-8  Cl H SOMe 5-9  Cl H SO₂Me 5-10  Cl H SO₂CH₂Cl 5-11  Cl H SEt 5-12  Cl H SO₂Et 5-13  Cl H CF₃ 5-14  Cl H NO₂ 5-15  Cl H pyrazol-1-yl 5-16  Cl H 1H-1,2,4- triazol-1-yl 5-17  Br H Cl 5-18  Br H Br 5-19  Br H SO₂Me 5-20  Br H SO₂Et 5-21  Br H CF₃ 5-22  SO₂Me H Cl 5-23  SO₂Me H Br 5-24  SO₂Me H SMe 5-25  SO₂Me H SOMe 5-26  SO₂Me H SO₂Me 5-27  SO₂Me H SO₂Et 5-28  SO₂Me H CF₃ 5-29  SO₂Et H Cl 5-30  SO₂Et H Br 5-31  SO₂Et H SMe 5-32  SO₂Et H SOMe 5-33  SO₂Et H SO₂Me 5-34  SO₂Et H CF₃ 5-35  NO₂ H F 5-36  NO₂ H Cl 5-37  NO₂ H Br 5-38  NO₂ H I 5-39  NO₂ H CN 5-40  NO₂ H SO₂Me 5-41  NO₂ H SO₂Et 5-42  NO₂ H CF₃ 5-43  Me H Cl 5-44  Me H Br 5-45  Me H SMe 5-46  Me H SO₂Me 5-47  Me H SO₂CH₂Cl 5-48  Me H SEt 5-49  Me H SO₂Et 5-50  Me H CF₃ 5-51  CH₂SO₂Me H CF₃ 5-52  Et H Cl 5-53  Et H Br 5-54  Et H SMe 5-55  Et H SO₂Me 5-56  Et H SO₂CH₂Cl 5-57  Et H SEt 5-58  Et H SO₂Et 5-59  Et H CF₃ 5-60  CF₃ H Cl 5-61  CF₃ H Br 5-62  CF₃ H SO₂Me 5-63  CF₃ H SO₂Et 5-64  CF₃ H CF₃ 5-65  NO₂ NH₂ F 5-66  NO₂ NHMe F 5-67  NO₂ NMe₂ F 5-68  NO₂ Me Cl 5-69  NO₂ NH₂ Cl 5-70  NO₂ NHMe Cl 5-71  NO₂ NMe₂ Cl 5-72  NO₂ NH₂ Br 5-73  NO₂ NHMe Br 5-74  NO₂ NMe₂ Br 5-75  NO₂ NH₂ CF₃ 5-76  NO₂ NMe₂ CF₃ 5-77  NO₂ NH₂ SO₂Me 5-78  NO₂ NH₂ SO₂Et 5-79  NO₂ NHMe SO₂Me 5-80  NO₂ NMe₂ SO₂Me 5-81  NO₂ NMe₂ SO₂Et 5-82  NO₂ NH₂ 1H-1,2,4- triazol-1-yl 5-83  NO₂ NHMe 1H-1,2,4- triazol-1-yl 5-84  NO₂ NMe₂ 1H-1,2,4- triazol-1-yl 5-85  Me SMe H 5-86  Me SOMe H 5-87  Me SO₂Me H 5-88  Me SEt H 5-89  Me SOEt H 5-90  Me SO₂Et H 5-91  Me S(CH₂)₂OMe H 5-92  Me SO(CH₂)₂OMe H 5-93  Me SO₂(CH₂)₂OMe H 5-94  Me F F 5-95  Me F Cl 5-96  Me SEt F 5-97  Me SOEt F 5-98  Me SO₂Et F 5-99  Me Me Cl 5-100 Me F Cl 5-101 Me Cl Cl 5-102 Me NH₂ Cl 5-103 Me NHMe Cl 5-104 Me NMe₂ Cl 5-105 Me O(CH₂)₂OMe Cl 5-106 Me O(CH₂)₃OMe Cl 5-107 Me O(CH₂)₄OMe Cl 5-108 Me OCH₂CONMe₂ Cl 5-109 Me O(CH₂)₂—CO—NMe₂ Cl 5-110 Me O(CH₂)₂—NH(CO)NMe₂ Cl 5-111 Me O(CH₂)₂—NH(CO)NHCO₂Et Cl 5-112 Me O(CH₂)₂—NHCO₂Me Cl 5-113 Me OCH₂—NHSO₂cPr Cl 5-114 Me O(CH₂)-5-2,4-dimethyl- Cl 2,4-dihydro-3H-1,2,4- triazol-3-one 5-115 Me O(CH₂)-3,5-dimethyl-1,2- Cl oxazol-4-yl 5-116 Me SMe Cl 5-117 Me SOMe Cl 5-118 Me SO₂Me Cl 5-119 Me SEt Cl 5-120 Me SOEt Cl 5-121 Me SO₂Et Cl 5-122 Me S(CH₂)₂OMe Cl 5-123 Me SO(CH₂)₂OMe Cl 5-124 Me SO₂(CH₂)₂OMe Cl 5-125 Me NH₂ Br 5-126 Me NHMe Br 5-127 Me NMe₂ Br 5-128 Me OCH₂(CO)NMe₂ Br 5-129 Me O(CH₂)-5-pyrrolidin-2- Br one 5-130 Me SMe Br 5-131 Me SOMe Br 5-132 Me SO₂Me Br 5-133 Me SEt Br 5-134 Me SOEt Br 5-135 Me SO₂Et Br 5-136 Me SMe I 5-137 Me SOMe I 5-138 Me SO₂Me I 5-139 Me SEt I 5-140 Me SOEt I 5-141 Me SO₂Et I 5-142 Me Cl CF₃ 5-143 Me SMe CF₃ 5-144 Me SOMe CF₃ 5-145 Me SO₂Me CF₃ 5-146 Me SEt CF₃ 5-147 Me SOEt CF₃ 5-148 Me SO₂Et CF₃ 5-149 Me S(CH₂)₂OMe CF₃ 5-150 Me SO(CH₂)₂OMe CF₃ 5-151 Me SO₂(CH₂)₂OMe CF₃ 5-152 Me Me SO₂Me 5-153 Me 4,5-dihydro-1,2-oxazol- SO₂Me 3-yl 5-154 Me 4,5-dihydro-1,2-oxazol-3- SO₂Et yl 5-155 Me 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 5-156 Me 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-157 Me NH₂ SO₂Me 5-158 Me NHMe SO₂Me 5-159 Me NMe₂ SO₂Me 5-160 Me NH(CH₂)₂OMe SO₂Me 5-161 Me pyrazol-1-yl SO₂Me 5-162 Me OH SO₂Me 5-163 Me OMe SO₂Me 5-164 Me OMe SO₂Et 5-165 Me OEt SO₂Me 5-166 Me OEt SO₂Et 5-167 Me OiPr SO₂Me 5-168 Me OiPr SO₂Et 5-169 Me O(CH₂)₂OMe SO₂Me 5-170 Me O(CH₂)₂OMe SO₂Et 5-171 Me O(CH₂)₃OMe SO₂Me 5-172 Me O(CH₂)₃OMe SO₂Et 5-173 Me O(CH₂)₄OMe SO₂Me 5-174 Me O(CH₂)₄OMe SO₂Et 5-175 Me O(CH₂)₂NHSO2Me SO₂Me 5-176 Me O(CH₂)₂NHSO2Me SO₂Et 5-177 Me OCH₂(CO)NMe₂ SO₂Me 5-178 Me OCH₂(CO)NMe₂ SO₂Et 5-179 Me [1,4]dioxan-2-yl-methoxy SO₂Me 5-180 Me [1,4]dioxan-2-yl-methoxy SO₂Et 5-181 Me O(CH₂)₂—O-(3,5-di SO₂Me methoxypyrimidin-2-yl) 5-182 Me Cl SO₂Me 5-183 Me SMe SO₂Me 5-184 Me SOMe SO₂Me 5-185 Me SO₂Me SO₂Me 5-186 Me SO₂Me SO₂Et 5-187 Me SEt SO₂Me 5-188 Me SOEt SO₂Me 5-189 Me SO₂Et SO₂Me 5-190 Me S(CH₂)₂OMe SO₂Me 5-191 Me SO(CH₂)₂OMe SO₂Me 5-192 Me SO₂(CH₂)₂OMe SO2Me 5-193 CH₂SMe OMe SO₂Me 5-194 CH₂OMe OMe SO₂Me 5-195 CH₂O(CH₂)₂OMe NH(CH₂)₂OEt SO₂Me 5-196 CH₂O(CH₂)₂OMe NH(CH₂)₃OEt SO₂Me 5-197 CH₂O(CH₂)₃OMe OMe SO₂Me 5-198 CH₂O(CH₂)₂OMe NH(CH₂)₂OMe SO₂Me 5-199 CH₂O(CH₂)₂OMe NH(CH₂)₃OMe SO₂Me 5-200 Et SMe Cl 5-201 Et SO₂Me Cl 5-202 Et SMe CF₃ 5-203 Et SO₂Me CF₃ 5-204 Et F SO₂Me 5-205 Et NH(CH₂)₂OMe SO₂Me 5-206 iPr SO₂Me CF₃ 5-207 cPr SO₂Me CF₃ 5-208 CF₃ O(CH₂)₂OMe F 5-209 CF₃ O(CH₂)₃OMe F 5-210 CF₃ OCH₂CONMe₂ F 5-211 CF₃ [1,4]dioxan-2-yl-methoxy F 5-212 CF₃ O(CH₂)₂OMe Cl 5-213 CF₃ O(CH₂)₃OMe Cl 5-214 CF₃ OCH₂CONMe₂ Cl 5-215 CF₃ [1,4]dioxan-2-yl-methoxy Cl 5-216 CF₃ O(CH₂)₂OMe Br 5-217 CF₃ O(CH₂)₃OMe Br 5-218 CF₃ OCH₂CONMe₂ Br 5-219 CF₃ [1,4]dioxan-2-yl-methoxy Br 5-220 CF₃ O(CH₂)₂OMe I 5-221 CF₃ O(CH₂)₃OMe I 5-222 CF₃ OCH₂CONMe₂ I 5-223 CF₃ [1,4]dioxan-2-yl-methoxy I 5-224 CF₃ F SO₂Me 5-225 CF₃ F SO₂Et 5-226 CF₃ O(CH₂)₂OMe SO₂Me 5-227 CF₃ O(CH₂)₂OMe SO₂Et 5-228 CF₃ O(CH₂)₃OMe SO₂Me 5-229 CF₃ O(CH₂)₃OMe SO₂Et 5-230 CF₃ OCH₂CONMe₂ SO₂Me 5-231 CF₃ OCH₂CONMe₂ SO₂Et 5-232 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Me 5-233 CF₃ [1,4]dioxan-2-yl-methoxy SO₂Et 5-234 F SMe CF₃ 5-235 F SOMe CF₃ 5-236 Cl Me Cl 5-237 Cl OCH₂CHCH₂ Cl 5-238 Cl OCH₂CHF₂ Cl 5-239 Cl O(CH₂)₂OMe Cl 5-240 Cl OCH₂CONMe₂ Cl 5-241 Cl O(CH₂)-5-pyrrolidin-2-one Cl 5-242 Cl SMe Cl 5-243 Cl SOMe Cl 5-244 Cl SO₂Me Cl 5-245 Cl F SMe 5-246 Cl Cl SO₂Me 5-247 Cl COOMe SO₂Me 5-248 Cl CONMe₂ SO₂Me 5-249 Cl CONMe(OMe) SO₂Me 5-250 Cl CH₂OMe SO₂Me 5-251 Cl CH₂OMe SO₂Et 5-252 Cl CH₂OEt SO₂Me 5-253 Cl CH₂OEt SO₂Et 5-254 Cl CH₂OCH₂CHF₂ SO₂Me 5-255 Cl CH₂OCH₂CF₃ SO₂Me 5-256 Cl CH₂OCH₂CF₃ SO₂Et 5-257 Cl CH₂OCH₂CF₂CHF₂ SO₂Me 5-258 Cl CH₂cPentyl SO₂Me 5-259 Cl CH₂PO(OMe)₂ SO₂Me 5-260 Cl 4,5-dihydro-1,2-oxazol-3-yl SMe 5-261 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Me 5-262 Cl 4,5-dihydro-1,2-oxazol-3-yl SO₂Et 5-263 Cl 5-cyanomethyl-4,5- SO₂Me dihydro-1,2-oxazol-3-yl 5-264 Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-265 Cl 5-(methoxymethyl)-4,5- SO₂Et dihydro-1,2-oxazol-3-yl 5-266 Cl 5-(methoxymethyl)-5-methyl- SO₂Et 4,5-dihydro-1,2-oxazol-3-yl 5-267 Cl CH₂O-tetrahydrofuran-3-yl SO₂Me 5-268 Cl CH₂O-tetrahydrofuran-3-yl SO₂Et 5-269 Cl CH₂OCH₂-tetrahydrofuran- SO₂Me 2-yl 5-270 Cl CH₂OCH₂-tetrahydrofuran- SO₂Et 2-yl 5-271 Cl CH₂OCH₂-tetrahydrofuran- SO₂Me 3-yl 5-272 Cl CH₂OCH₂-tetrahydrofuran- SO₂Et 3-yl 5-273 Cl OMe SO₂Me 5-274 Cl OMe SO₂Et 5-275 Cl OEt SO₂Me 5-276 Cl OEt SO₂Et 5-277 Cl OiPr SO₂Me 5-278 Cl OiPr SO₂Et 5-279 Cl O(CH₂)₂OMe SO₂Me 5-280 Cl O(CH₂)₄OMe SO₂Me 5-281 Cl O(CH₂)₄OMe SO₂Et 5-282 Cl O(CH₂)₃OMe SO₂Me 5-283 Cl O(CH₂)₃OMe SO₂Et 5-284 Cl O(CH₂)₂OMe SO₂Me 5-285 Cl O(CH₂)₂OMe SO₂Et 5-286 Cl [1,4]dioxan-2-yl-methoxy SO₂Me 5-287 Cl [1,4]dioxan-2-yl-methoxy SO₂Et 5-288 Cl OCH₂(CO)NMe₂ SO₂Me 5-289 Cl OCH₂(CO)NMe₂ SO₂Et 5-290 Cl SMe SO₂Me 5-291 Cl SOMe SO₂Me 5-292 Br OMe Br 5-293 Br O(CH₂)₂OMe Br 5-294 Br O(CH₂)₂OMe SO₂Me 5-295 Br O(CH₂)₂OMe SO₂Et 5-296 Br O(CH₂)₃OMe SO₂Me 5-297 Br O(CH₂)₃OMe SO₂Et 5-298 Br O(CH₂)₄OMe SO₂Me 5-299 Br O(CH₂)₄OMe SO₂Et 5-300 Br [1,4]dioxan-2-yl-methoxy SO₂Me 5-301 Br [1,4]dioxan-2-yl-methoxy SO₂Et 5-302 I O(CH₂)₂OMe SO₂Me 5-303 I O(CH₂)₂OMe SO₂Et 5-304 I O(CH₂)₃OMe SO₂Me 5-305 I O(CH₂)₃OMe SO₂Et 5-306 I O(CH₂)₄OMe SO₂Me 5-307 I O(CH₂)₄OMe SO₂Et 5-308 I [1,4]dioxan-2-yl-methoxy SO₂Me 5-309 I [1,4]dioxan-2-yl-methoxy SO₂Et 5-310 OMe SMe CF₃ 5-311 OMe SOMe CF₃ 5-312 OMe SO₂Me CF₃ 5-313 OMe SOEt CF₃ 5-314 OMe SO₂Et CF₃ 5-315 OMe S(CH₂)₂OMe CF₃ 5-316 OMe SO(CH₂)₂OMe CF₃ 5-317 OMe SO₂(CH₂)₂OMe CF₃ 5-318 OMe SMe Cl 5-319 OMe SOMe Cl 5-320 OMe SO₂Me Cl 5-321 OMe SEt Cl 5-322 OMe SOEt Cl 5-323 OMe SO2Et Cl 5-324 OMe S(CH₂)₂OMe Cl 5-325 OMe SO(CH₂)₂OMe Cl 5-326 OMe SO₂(CH₂)₂OMe Cl 5-327 OMe H SO₂Me 5-328 OCH₂-c-Pr SMe CF₃ 5-329 OCH₂-c-Pr SOMe CF₃ 5-330 OCH₂-c-Pr SO₂Me CF₃ 5-331 OCH₂-c-Pr SEt CF₃ 5-332 OCH₂-c-Pr SOEt CF₃ 5-333 OCH₂-c-Pr SO₂Et CF₃ 5-334 OCH₂-c-Pr S(CH₂)₂OMe CF₃ 5-335 OCH₂-c-Pr SO(CH₂)₂OMe CF₃ 5-336 OCH₂-c-Pr SO₂(CH₂)₂OMe CF₃ 5-337 OCH₂-c-Pr SMe Cl 5-338 OCH₂-c-Pr SOMe Cl 5-339 OCH₂-c-Pr SO₂Me Cl 5-340 OCH₂-c-Pr SEt Cl 5-341 OCH₂-c-Pr SOEt Cl 5-342 OCH₂-c-Pr SO₂Et Cl 5-343 OCH₂-c-Pr S(CH₂)₂OMe Cl 5-344 OCH₂-c-Pr SO(CH₂)₂OMe Cl 5-345 OCH₂-c-Pr SO₂(CH₂)₂OMe Cl 5-346 OCH₂-c-Pr SMe SO₂Me 5-347 OCH₂-c-Pr SOMe SO₂Me 5-348 OCH₂-c-Pr SO₂Me SO₂Me 5-349 OCH₂-c-Pr SEt SO₂Me 5-350 OCH₂-c-Pr SOEt SO₂Me 5-351 OCH₂-c-Pr SO₂Et SO₂Me 5-352 OCH₂-c-Pr S(CH₂)₂OMe SO₂Me 5-353 OCH₂-c-Pr SO(CH₂)₂OMe SO₂Me 5-354 OCH₂-c-Pr SO₂(CH₂)₂OMe SO₂Me 5-355 SO₂Me F CF₃ 5-356 SO₂Me NH₂ CF₃ 5-357 SO₂Me NHEt Cl 5-358 SMe SEt F 5-359 SMe SMe F 5-360 F SO₂Me CF₃ 5-361 Cl SMe CF₃ 5-362 Cl S(O)Me CF₃ 5-363 Cl SO₂Me CF₃ 5-364 Cl SO₂Me SO₂Me

TABLE 6 Compounds of the general formula (I) in which A is CY, and R, X, Y, and Z are as defined below.

No. R X Y Z 6-1   c-Pr NO₂ H SO₂Me 6-2   c-Pr Cl H SO₂Me 6-3   c-Pr SO₂Me H CF₃ 6-4   c-Pr NO₂ H OMe 6-5   c-Pr NO₂ H Br 6-6   c-Pr NO₂ H Cl 6-7   c-Pr NO₂ H CF₃ 6-8   c-Pr NO₂ H NO₂ 6-9   c-Pr NO₂ H Me 6-10  c-Pr NO₂ H F 6-11  c-Pr OMe H SO₂Me 6-12  c-Pr CF₃ H NO₂ 6-13  c-Pr CF₃ H Cl 6-14  c-Pr CH₂SO₂Me H Br 6-15  c-Pr Cl CH₂OCH₂CF₃ SO₂Me 6-16  c-Pr Cl CH₂OCH₂CF₃ SMe 6-17  c-Pr Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 6-18  c-Pr Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-19  c-Pr Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-20  c-Pr Cl SMe Cl 6-21  c-Pr Cl SMe SO₂Me 6-22  c-Pr Cl Me SO₂Et 6-23  c-Pr Cl O(CH₂)₂OMe Cl 6-24  c-Pr Cl OCH₂-cyclopropyl Cl 6-25  c-Pr Cl OMe Cl 6-26  c-Pr Cl NHAc Cl 6-27  c-Pr Cl OCH₂C(O)NMe₂ Cl 6-28  c-Pr Cl Cl SO₂Me 6-29  c-Pr Cl pyrazol-1-yl SO₂Me 6-30  c-Pr Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-31  c-Pr Cl 1,2,3-triazol-1-yl SO₂Me 6-32  c-Pr Cl 1,2,3-triazol-2-yl SO₂Me 6-33  c-Pr Cl F SO₂Me 6-34  c-Pr Me SO₂Me SO₂Me 6-35  c-Pr Me SO₂Me CF₃ 6-36  c-Pr Me NMe₂ SO₂Me 6-37  c-Pr Me S(O)Me CF₃ 6-38  c-Pr Me SMe CF₃ 6-39  c-Pr Me SO₂CH₂CH₂OMe CF₃ 6-40  c-Pr Me pyrazol-1-yl SO₂Me 6-41  c-Pr Me 4-methoxy- SO₂Me pyrazol-1-yl 6-42  c-Pr Me 1,2,3-triazol-1-yl SO₂Me 6-43  c-Pr Me 1,2,3-triazol-2-yl SO₂Me 6-44  c-Pr Me Cl SO₂Me 6-45  c-Pr Me Me SO₂Me 6-46  c-Pr Me F Cl 6-47  c-Pr Me SO₂Me Cl 6-48  c-Pr Me NMe₂ SO₂Me 6-49  c-Pr Me NH(CH₂)₂OMe SO₂Me 6-50  c-Pr CF₃ F SO₂CH₃ 6-51  c-Pr CF₃ SMe SO₂CH₃ 6-52  c-Pr CF₃ SEt SO₂CH₃ 6-53  c-Pr CF₃ S(O)Et SO₂CH₃ 6-54  c-Pr CF₃ SO₂CH₃ SO₂CH₃ 6-55  c-Pr CF₃ OCH₂CH₂OMe SO₂CH₃ 6-56  c-Pr CF₃ OCH₂(CO)NMe₂ SO2Me 6-57  c-Pr CF₃ CH₂O-tetrahydrofuran- SO₂Et 2-yl 6-58  c-Pr SMe SMe F 6-59  c-Pr SMe SEt F 6-60  c-Pr SO₂CH₃ F Cl 6-61  c-Pr F S(O)Me CF₃ 6-62  c-Pr F SMe CF₃ 6-63  CO₂Et NO₂ H SO₂Me 6-64  CO₂Et Cl H SO₂Me 6-65  CO₂Et SO₂Me H CF₃ 6-66  CO₂Et NO₂ H OMe 6-67  CO₂Et NO₂ H Br 6-68  CO₂Et NO₂ H CF₃ 6-69  CO₂Et NO₂ H NO₂ 6-70  CO₂Et NO₂ H Cl 6-71  CO₂Et NO₂ H Me 6-72  CO₂Et NO₂ H F 6-73  CO₂Et OMe H SO₂Me 6-74  CO₂Et CF₃ H NO₂ 6-75  CO₂Et CH₂SO₂Me H Br 6-76  CO₂Et Cl CH₂OCH₂CF₃ SO₂Me 6-77  CO₂Et Cl CH₂OCH₂CF₃ SMe 6-78  CO₂Et Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-79  CO₂Et Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-80  CO₂Et Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-81  CO₂Et Cl SMe Cl 6-82  CO₂Et Cl SMe SO₂Me 6-83  CO₂Et Cl Me SO₂Et 6-84  CO₂Et Cl O(CH₂)₂OMe Cl 6-85  CO₂Et Cl OCH₂-cyclopropyl Cl 6-86  CO₂Et Cl OMe Cl 6-87  CO₂Et Cl NHAc Cl 6-88  CO₂Et Cl OCH₂C(O)NMe₂ Cl 6-89  CO₂Et Cl Cl SO₂Me 6-90  CO₂Et Cl pyrazol-1-yl SO₂Me 6-91  CO₂Et Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-92  CO₂Et Cl 1,2,3-triazol-1-yl SO₂Me 6-93  CO₂Et Cl 1,2,3-triazol-2-yl SO₂Me 6-94  CO₂Et Cl F SO₂Me 6-95  CO₂Et Me SO₂Me SO₂Me 6-96  CO₂Et Me SO₂Me CF₃ 6-97  CO₂Et Me NMe₂ SO₂Me 6-98  CO₂Et Me S(O)Me CF₃ 6-99  CO₂Et Me SMe CF₃ 6-100  CO₂Et Me SO₂CH₂CH₂OMe CF₃ 6-101  CO₂Et Me pyrazol-1-yl SO₂Me 6-102  CO₂Et Me 4-methoxy- SO₂Me pyrazol-1-yl 6-103  CO₂Et Me 1,2,3-triazol-1-yl SO₂Me 6-104  CO₂Et Me 1,2,3-triazol-2-yl SO₂Me 6-105  CO₂Et Me Cl SO₂Me 6-106  CO₂Et Me Me SO₂Me 6-107  CO₂Et Me Me SMe 6-108  CO₂Et Me SO₂Me Cl 6-109  CO₂Et Me NMe₂ SO₂Me 6-110  CO₂Et Me NH(CH₂)₂OMe SO₂Me 6-111  CO₂Et CF₃ F SO₂CH₃ 6-112  CO₂Et CF₃ SMe SO₂CH₃ 6-113  CO₂Et CF₃ SEt SO₂CH₃ 6-114  CO₂Et CF₃ S(O)Et SO₂CH₃ 6-115  CO₂Et CF₃ SO₂CH₃ SO₂CH₃ 6-116  CO₂Et CF₃ OCH₂CH₂OMe SO₂CH₃ 6-117  CO₂Et CF₃ OCH₂(CO)NMe₂ SO2Me 6-118  CO₂Et CF₃ CH₂O-tetrahydrofuran- SO₂Et 2-yl 6-119  CO₂Et SMe SMe F 6-120  CO₂Et SMe SEt F 6-121  CO₂Et SO₂CH₃ F Cl 6-122  CO₂Et F S(O)Me CF₃ 6-123  CO₂Et F SMe CF₃ 6-124  CO₂Me NO₂ H SO₂Me 6-125  CO₂Me Cl H SO₂Me 6-126  CO₂Me SO₂Me H CF₃ 6-127  CO₂Me NO₂ H OMe 6-128  CO₂Me NO₂ H Br 6-129  CO₂Me NO₂ H CF₃ 6-130  CO₂Me NO₂ H NO₂ 6-131  CO₂Me NO₂ H Cl 6-132  CO₂Me NO₂ H Me 6-133  CO₂Me NO₂ H F 6-134  CO₂Me OMe H SO₂Me 6-135  CO₂Me CF₃ H NO₂ 6-136  CO₂Me CH₂SO₂Me H Br 6-137  CO₂Me Cl CH₂OCH₂CF₃ SO₂Me 6-138  CO₂Me Cl CH₂OCH₂CF₃ SMe 6-139  CO₂Me Cl 5-cyanomethyl- SO₂Et 4,5-dihydro-1,2- oxazol-3-yl 6-140  CO₂Me Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-141  CO₂Me Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-142  CO₂Me Cl SMe Cl 6-143  CO₂Me Cl SMe SO₂Me 6-144  CO₂Me Cl Me SO₂Et 6-145  CO₂Me Cl O(CH₂)₂OMe Cl 6-146  CO₂Me Cl OCH₂-cyclopropyl Cl 6-147  CO₂Me Cl OMe Cl 6-148  CO₂Me Cl NHAc Cl 6-149  CO₂Me Cl OCH₂C(O)NMe₂ Cl 6-150  CO₂Me Cl Cl SO₂Me 6-151  CO₂Me Cl pyrazol-1-yl SO₂Me 6-152  CO₂Me Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-153  CO₂Me Cl 1,2,3-triazol-1-yl SO₂Me 6-154  CO₂Me Cl 1,2,3-triazol-2-yl SO₂Me 6-155  CO₂Me Cl F SO₂Me 6-156  CO₂Me Me SO₂Me SO₂Me 6-157  CO₂Me Me SO₂Me CF₃ 6-158  CO₂Me Me NMe₂ SO₂Me 6-159  CO₂Me Me S(O)Me CF₃ 6-160  CO₂Me Me SMe CF₃ 6-161  CO₂Me Me SO₂CH₂CH₂OMe CF₃ 6-162  CO₂Me Me pyrazol-1-yl SO₂Me 6-163  CO₂Me Me 4-methoxy- SO₂Me pyrazol-1-yl 6-164  CO₂Me Me 1,2,3-triazol-1-yl SO₂Me 6-165  CO₂Me Me 1,2,3-triazol-2-yl SO₂Me 6-166  CO₂Me Me Cl SO₂Me 6-167  CO₂Me Me Me SO₂Me 6-168  CO₂Me Me Me SMe 6-169  CO₂Me Me SO₂Me Cl 6-170  CO₂Me Me NMe₂ SO₂Me 6-171  CO₂Me Me NH(CH₂)₂OMe SO₂Me 6-172  CO₂Me CF₃ F SO₂CH₃ 6-173  CO₂Me CF₃ SMe SO₂CH₃ 6-174  CO₂Me CF₃ SEt SO₂CH₃ 6-175  CO₂Me CF₃ S(O)Et SO₂CH₃ 6-176  CO₂Me CF₃ SO₂CH₃ SO₂CH₃ 6-177  CO₂Me CF₃ OCH₂CH₂OMe SO₂CH₃ 6-178  CO₂Me CF₃ OCH₂(CO)NMe₂ SO2Me 6-179  CO₂Me CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-180  CO₂Me SMe SMe F 6-181  CO₂Me SMe SEt F 6-182  CO₂Me SO₂CH₃ F Cl 6-183  CO₂Me F S(O)Me CF₃ 6-184  CO₂Me F SMe CF₃ 6-185  benzyl NO₂ H SO₂Me 6-186  benzyl Cl H SO₂Me 6-187  benzyl SO₂Me H CF₃ 6-188  benzyl NO₂ H OMe 6-189  benzyl NO₂ H Br 6-190  benzyl NO₂ H CF₃ 6-191  benzyl NO₂ H NO₂ 6-192  benzyl NO₂ H Cl 6-193  benzyl NO₂ H Me 6-194  benzyl NO₂ H F 6-195  benzyl OMe H SO₂Me 6-196  benzyl CF₃ H NO₂ 6-197  benzyl CH₂SO₂Me H Br 6-198  benzyl Cl CH₂OCH₂CF₃ SO₂Me 6-199  benzyl Cl CH₂OCH₂CF₃ SMe 6-200  benzyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-201  benzyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-202  benzyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2- yl 6-203  benzyl Cl SMe Cl 6-204  benzyl Cl SMe SO₂Me 6-205  benzyl Cl Me SO₂Et 6-206  benzyl Cl O(CH₂)₂OMe Cl 6-207  benzyl Cl OCH₂-cyclopropyl Cl 6-208  benzyl Cl OMe Cl 6-209  benzyl Cl NHAc Cl 6-210  benzyl Cl OCH₂C(O)NMe₂ Cl 6-211  benzyl Cl Cl SO₂Me 6-212  benzyl Cl pyrazol-1-yl SO₂Me 6-213  benzyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-214  benzyl Cl 1,2,3-triazol-1-yl SO₂Me 6-215  benzyl Cl 1,2,3-triazol-2-yl SO₂Me 6-216  benzyl Cl F SO₂Me 6-217  benzyl Me SO₂Me SO₂Me 6-218  benzyl Me SO₂Me CF₃ 6-219  benzyl Me NMe₂ SO₂Me 6-220  benzyl Me S(O)Me CF₃ 6-221  benzyl Me SMe CF₃ 6-222  benzyl Me SO₂CH₂CH₂OMe CF₃ 6-223  benzyl Me pyrazol-1-yl SO₂Me 6-224  benzyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-225  benzyl Me 1,2,3-triazol-1-yl SO₂Me 6-226  benzyl Me 1,2,3-triazol-2-yl SO₂Me 6-227  benzyl Me Cl SO₂Me 6-228  benzyl Me Me SO₂Me 6-229  benzyl Me Me SMe 6-230  benzyl Me SO₂Me Cl 6-231  benzyl Me NMe₂ SO₂Me 6-232  benzyl Me NH(CH₂)₂OMe SO₂Me 6-233  benzyl CF₃ F SO₂CH₃ 6-234  benzyl CF₃ SMe SO₂CH₃ 6-235  benzyl CF₃ SEt SO₂CH₃ 6-236  benzyl CF₃ S(O)Et SO₂CH₃ 6-237  benzyl CF₃ SO₂CH₃ SO₂CH₃ 6-238  benzyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-239  benzyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-240  benzyl CF₃ CH₂O-tetrahydrofuran- SO₂Et 2-yl 6-241  benzyl SMe SMe F 6-242  benzyl SMe SEt F 6-243  benzyl SO₂CH₃ F Cl 6-244  benzyl F S(O)Me CF₃ 6-245  benzyl F SMe CF₃ 6-246  phenyl NO₂ H SO₂Me 6-247  phenyl Cl H SO₂Me 6-248  phenyl SO₂Me H CF₃ 6-249  phenyl NO₂ H OMe 6-250  phenyl NO₂ H Br 6-251  phenyl NO₂ H CF₃ 6-252  phenyl NO₂ H NO₂ 6-253  phenyl NO₂ H Cl 6-254  phenyl NO₂ H Me 6-255  phenyl NO₂ H F 6-256  phenyl OMe H SO₂Me 6-257  phenyl CF₃ H NO₂ 6-258  phenyl CH₂SO₂Me H Br 6-259  phenyl Cl CH₂OCH₂CF₃ SO₂Me 6-260  phenyl Cl CH₂OCH₂CF₃ SMe 6-261  phenyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-262  phenyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-263  phenyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2- yl 6-264  phenyl Cl SMe Cl 6-265  phenyl Cl SMe SO₂Me 6-266  phenyl Cl Me SO₂Et 6-267  phenyl Cl O(CH₂)₂OMe Cl 6-268  phenyl Cl OCH₂-cyclopropyl Cl 6-269  phenyl Cl OMe Cl 6-270  phenyl Cl NHAc Cl 6-271  phenyl Cl OCH₂C(O)NMe₂ Cl 6-272  phenyl Cl Cl SO₂Me 6-273  phenyl Cl pyrazol-1-yl SO₂Me 6-274  phenyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-275  phenyl Cl 1,2,3-triazol-1-yl SO₂Me 6-276  phenyl Cl 1,2,3-triazol-2-yl SO₂Me 6-277  phenyl Cl F SO₂Me 6-278  phenyl Me SO₂Me SO₂Me 6-279  phenyl Me SO₂Me CF₃ 6-280  phenyl Me NMe₂ SO₂Me 6-281  phenyl Me S(O)Me CF₃ 6-282  phenyl Me SMe CF₃ 6-283  phenyl Me SO₂CH₂CH₂OMe CF₃ 6-284  phenyl Me pyrazol-1-yl SO₂Me 6-285  phenyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-286  phenyl Me 1,2,3-triazol-1-yl SO₂Me 6-287  phenyl Me 1,2,3-triazol-2-yl SO₂Me 6-288  phenyl Me Cl SO₂Me 6-289  phenyl Me Me SO₂Me 6-290  phenyl Me Me SMe 6-291  phenyl Me SO₂Me Cl 6-292  phenyl Me NMe₂ SO₂Me 6-293  phenyl Me NH(CH₂)₂OMe SO₂Me 6-294  phenyl CF₃ F SO₂CH₃ 6-295  phenyl CF₃ SMe SO₂CH₃ 6-296  phenyl CF₃ SEt SO₂CH₃ 6-297  phenyl CF₃ S(O)Et SO₂CH₃ 6-298  phenyl CF₃ SO₂CH₃ SO₂CH₃ 6-299  phenyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-300  phenyl CF₃ OCH₂(CO)NMe₂ SO₂Me 6-301  phenyl CF₃ CH₂O-tetrahydrofuran- SO₂Et 2-yl 6-302  phenyl SMe SMe F 6-303  phenyl SMe SEt F 6-304  phenyl SO₂CH₃ F Cl 6-305  phenyl F S(O)Me CF₃ 6-306  phenyl F SMe CF₃ 6-307  pyrazin-2-yl NO₂ H SO₂Me 6-308  pyrazin-2-yl Cl H SO₂Me 6-309  pyrazin-2-yl SO₂Me H CF₃ 6-310  pyrazin-2-yl NO₂ H OMe 6-311  pyrazin-2-yl NO₂ H Br 6-312  pyrazin-2-yl NO₂ H CF₃ 6-313  pyrazin-2-yl NO₂ H NO₂ 6-314  pyrazin-2-yl NO₂ H Cl 6-315  pyrazin-2-yl NO₂ H Me 6-316  pyrazin-2-yl NO₂ H F 6-317  pyrazin-2-yl OMe H SO₂Me 6-318  pyrazin-2-yl CF₃ H NO₂ 6-319  pyrazin-2-yl CH₂SO₂Me H Br 6-320  pyrazin-2-yl Cl CH₂OCH₂CF₃ SO₂Me 6-321  pyrazin-2-yl Cl CH₂OCH₂CF₃ SMe 6-322  pyrazin-2-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-323  pyrazin-2-yl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-324  pyrazin-2-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-325  pyrazin-2-yl Cl SMe Cl 6-326  pyrazin-2-yl Cl SMe SO₂Me 6-327  pyrazin-2-yl Cl Me SO₂Et 6-328  pyrazin-2-yl Cl O(CH₂)₂OMe Cl 6-329  pyrazin-2-yl Cl OCH₂-cyclopropyl Cl 6-330  pyrazin-2-yl Cl OMe Cl 6-331  pyrazin-2-yl Cl NHAc Cl 6-332  pyrazin-2-yl Cl OCH₂C(O)NMe₂ Cl 6-333  pyrazin-2-yl Cl Cl SO₂Me 6-334  pyrazin-2-yl Cl pyrazol-1-yl SO₂Me 6-335  pyrazin-2-yl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-336  pyrazin-2-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-337  pyrazin-2-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-338  pyrazin-2-yl Cl F SO₂Me 6-339  pyrazin-2-yl Me SO₂Me SO₂Me 6-340  pyrazin-2-yl Me SO₂Me CF₃ 6-341  pyrazin-2-yl Me NMe₂ SO₂Me 6-342  pyrazin-2-yl Me S(O)Me CF₃ 6-343  pyrazin-2-yl Me SMe CF₃ 6-344  pyrazin-2-yl Me SO₂CH₂CH₂OMe CF₃ 6-345  pyrazin-2-yl Me pyrazol-1-yl SO₂Me 6-346  pyrazin-2-yl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-347  pyrazin-2-yl Me 1,2,3-triazol-1-yl SO₂Me 6-348  pyrazin-2-yl Me 1,2,3-triazol-2-yl SO₂Me 6-349  pyrazin-2-yl Me Cl SO₂Me 6-350  pyrazin-2-yl Me Me SO₂Me 6-351  pyrazin-2-yl Me Me SMe 6-352  pyrazin-2-yl Me SO₂Me Cl 6-353  pyrazin-2-yl Me NMe₂ SO₂Me 6-354  pyrazin-2-yl Me NH(CH₂)₂OMe SO₂Me 6-355  pyrazin-2-yl CF₃ F SO₂CH₃ 6-356  pyrazin-2-yl CF₃ SMe SO₂CH₃ 6-357  pyrazin-2-yl CF₃ SEt SO₂CH₃ 6-358  pyrazin-2-yl CF₃ S(O)Et SO₂CH₃ 6-359  pyrazin-2-yl CF₃ SO₂CH₃ SO₂CH₃ 6-360  pyrazin-2-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-361  pyrazin-2-yl CF₃ OCH₂(CO)NMe₂ SO2Me 6-362  pyrazin-2-yl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-363  pyrazin-2-yl SMe SMe F 6-364  pyrazin-2-yl SMe SEt F 6-365  pyrazin-2-yl SO₂CH₃ F Cl 6-366  pyrazin-2-yl F S(O)Me CF₃ 6-367  pyrazin-2-yl F SMe CF₃ 6-368  4-OMe—Ph NO₂ H SO₂Me 6-369  4-OMe—Ph Cl H SO₂Me 6-370  4-OMe—Ph SO₂Me H CF₃ 6-371  4-OMe—Ph NO₂ H OMe 6-372  4-OMe—Ph NO₂ H Br 6-373  4-OMe—Ph NO₂ H CF₃ 6-374  4-OMe—Ph NO₂ H NO₂ 6-375  4-OMe—Ph NO₂ H Cl 6-376  4-OMe—Ph NO₂ H Me 6-377  4-OMe—Ph NO₂ H F 6-378  4-OMe—Ph OMe H SO₂Me 6-379  4-OMe—Ph CF₃ H NO₂ 6-380  4-OMe—Ph CH₂SO₂Me H Br 6-381  4-OMe—Ph Cl CH₂OCH₂CF₃ SO₂Me 6-382  4-OMe—Ph Cl CH₂OCH₂CF₃ SMe 6-383  4-OMe—Ph Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-384  4-OMe—Ph Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-385  4-OMe—Ph Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-386  4-OMe—Ph Cl SMe Cl 6-387  4-OMe—Ph Cl SMe SO₂Me 6-388  4-OMe—Ph Cl Me SO₂Et 6-389  4-OMe—Ph Cl O(CH₂)₂OMe Cl 6-390  4-OMe—Ph Cl OCH₂-cyclopropyl Cl 6-391  4-OMe—Ph Cl OMe Cl 6-392  4-OMe—Ph Cl NHAc Cl 6-393  4-OMe—Ph Cl OCH₂C(O)NMe₂ Cl 6-394  4-OMe—Ph Cl Cl SO₂Me 6-395  4-OMe—Ph Cl pyrazol-1-yl SO₂Me 6-396  4-OMe—Ph Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-397  4-OMe—Ph Cl 1,2,3-triazol-1-yl SO₂Me 6-398  4-OMe—Ph Cl 1,2,3-triazol-2-yl SO₂Me 6-399  4-OMe—Ph Cl F SO₂Me 6-400  4-OMe—Ph Me SO₂Me SO₂Me 6-401  4-OMe—Ph Me SO₂Me CF₃ 6-402  4-OMe—Ph Me NMe₂ SO₂Me 6-403  4-OMe—Ph Me S(O)Me CF₃ 6-404  4-OMe—Ph Me SMe CF₃ 6-405  4-OMe—Ph Me SO₂CH₂CH₂OMe CF₃ 6-406  4-OMe—Ph Me pyrazol-1-yl SO₂Me 6-407  4-OMe—Ph Me 4-methoxy- SO₂Me pyrazol-1-yl 6-408  4-OMe—Ph Me 1,2,3-triazol-1-yl SO₂Me 6-409  4-OMe—Ph Me 1,2,3-triazol-2-yl SO₂Me 6-410  4-OMe—Ph Me Cl SO₂Me 6-411  4-OMe—Ph Me Me SO₂Me 6-412  4-OMe—Ph Me Me SMe 6-413  4-OMe—Ph Me SO₂Me Cl 6-414  4-OMe—Ph Me NMe₂ SO₂Me 6-415  4-OMe—Ph Me NH(CH₂)₂OMe SO₂Me 6-416  4-OMe—Ph CF₃ F SO₂CH₃ 6-417  4-OMe—Ph CF₃ SMe SO₂CH₃ 6-418  4-OMe—Ph CF₃ SEt SO₂CH₃ 6-419  4-OMe—Ph CF₃ S(O)Et SO₂CH₃ 6-420  4-OMe—Ph CF₃ SO₂CH₃ SO₂CH₃ 6-421  4-OMe—Ph CF₃ OCH₂CH₂OMe SO₂CH₃ 6-422  4-OMe—Ph CF₃ OCH₂(CO)NMe₂ SO₂Me 6-423  4-OMe—Ph CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-424  4-OMe—Ph SMe SMe F 6-425  4-OMe—Ph SMe SEt F 6-426  4-OMe—Ph SO₂CH₃ F Cl 6-427  4-OMe—Ph F S(O)Me CF₃ 6-428  4-OMe—Ph F SMe CF₃ 6-429  4-Cl—Ph NO₂ H SO₂Me 6-430  4-Cl—Ph Cl H SO₂Me 6-431  4-Cl—Ph SO₂Me H CF₃ 6-432  4-Cl—Ph NO₂ H OMe 6-433  4-Cl—Ph NO₂ H Br 6-434  4-Cl—Ph NO₂ H CF₃ 6-435  4-Cl—Ph NO₂ H NO₂ 6-436  4-Cl—Ph NO₂ H Cl 6-437  4-Cl—Ph NO₂ H Me 6-438  4-Cl—Ph NO₂ H F 6-439  4-Cl—Ph OMe H SO₂Me 6-440  4-Cl—Ph CF₃ H NO₂ 6-441  4-Cl—Ph CH₂SO₂Me H Br 6-442  4-Cl—Ph Cl CH₂OCH₂CF₃ SO₂Me 6-443  4-Cl—Ph Cl CH₂OCH₂CF₃ SMe 6-444  4-Cl—Ph Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-445  4-Cl—Ph Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-446  4-Cl—Ph Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-447  4-Cl—Ph Cl SMe Cl 6-448  4-Cl—Ph Cl SMe SO₂Me 6-449  4-Cl—Ph Cl Me SO₂Et 6-450  4-Cl—Ph Cl O(CH₂)₂OMe Cl 6-451  4-Cl—Ph Cl OCH₂-cyclopropyl Cl 6-452  4-Cl—Ph Cl OMe Cl 6-453  4-Cl—Ph Cl NHAc Cl 6-454  4-Cl—Ph Cl OCH₂C(O)NMe₂ Cl 6-455  4-Cl—Ph Cl Cl SO₂Me 6-456  4-Cl—Ph Cl pyrazol-1-yl SO₂Me 6-457  4-Cl—Ph Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-458  4-Cl—Ph Cl 1,2,3-triazol-1-yl SO₂Me 6-459  4-Cl—Ph Cl 1,2,3-triazol-2-yl SO₂Me 6-460  4-Cl—Ph Cl F SO₂Me 6-461  4-Cl—Ph Me SO₂Me SO₂Me 6-462  4-Cl—Ph Me SO₂Me CF₃ 6-463  4-Cl—Ph Me NMe₂ SO₂Me 6-464  4-Cl—Ph Me S(O)Me CF₃ 6-465  4-Cl—Ph Me SMe CF₃ 6-466  4-Cl—Ph Me SO₂CH₂CH₂OMe CF₃ 6-467  4-Cl—Ph Me pyrazol-1-yl SO₂Me 6-468  4-Cl—Ph Me 4-methoxy- SO₂Me pyrazol-1-yl 6-469  4-Cl—Ph Me 1,2,3-triazol-1-yl SO₂Me 6-470  4-Cl—Ph Me 1,2,3-triazol-2-yl SO₂Me 6-471  4-Cl—Ph Me Cl SO₂Me 6-472  4-Cl—Ph Me Me SO₂Me 6-473  4-Cl—Ph Me Me SMe 6-474  4-Cl—Ph Me SO₂Me Cl 6-475  4-Cl—Ph Me NMe₂ SO₂Me 6-476  4-Cl—Ph Me NH(CH₂)₂OMe SO₂Me 6-477  4-Cl—Ph CF₃ F SO₂CH₃ 6-478  4-Cl—Ph CF₃ SMe SO₂CH₃ 6-479  4-Cl—Ph CF₃ SEt SO₂CH₃ 6-480  4-Cl—Ph CF₃ S(O)Et SO₂CH₃ 6-481  4-Cl—Ph CF₃ SO₂CH₃ SO₂CH₃ 6-482  4-Cl—Ph CF₃ OCH₂CH₂OMe SO₂CH₃ 6-483  4-Cl—Ph CF₃ OCH₂(CO)NMe₂ SO2Me 6-484  4-Cl—Ph CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-485  4-Cl—Ph SMe SMe F 6-486  4-Cl—Ph SMe SEt F 6-487  4-Cl—Ph SO₂CH₃ F Cl 6-488  4-Cl—Ph F S(O)Me CF₃ 6-489  4-Cl—Ph F SMe CF₃ 6-490  tert-butyl NO₂ H SO₂Me 6-491  tert-butyl Cl H SO₂Me 6-492  tert-butyl SO₂Me H CF₃ 6-493  tert-butyl NO₂ H OMe 6-494  tert-butyl NO₂ H Br 6-495  tert-butyl NO₂ H CF₃ 6-496  tert-butyl NO₂ H NO₂ 6-497  tert-butyl NO₂ H Cl 6-498  tert-butyl NO₂ H Me 6-499  tert-butyl NO₂ H F 6-500  tert-butyl OMe H SO₂Me 6-501  tert-butyl CF₃ H NO₂ 6-502  tert-butyl CH₂SO₂Me H Br 6-503  tert-butyl Cl CH₂OCH₂CF₃ SO₂Me 6-504  tert-butyl Cl CH₂OCH₂CF₃ SMe 6-505  tert-butyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-506  tert-butyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-507  tert-butyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-508  tert-butyl Cl SMe Cl 6-509  tert-butyl Cl SMe SO₂Me 6-510  tert-butyl Cl Me SO₂Et 6-511  tert-butyl Cl O(CH₂)₂OMe Cl 6-512  tert-butyl Cl OCH₂-cyclopropyl Cl 6-513  tert-butyl Cl OMe Cl 6-514  tert-butyl Cl NHAc Cl 6-515  tert-butyl Cl OCH₂C(O)NMe₂ Cl 6-516  tert-butyl Cl Cl SO₂Me 6-517  tert-butyl Cl pyrazol-1-yl SO₂Me 6-518  tert-butyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-519  tert-butyl Cl 1,2,3-triazol-1-yl SO₂Me 6-520  tert-butyl Cl 1,2,3-triazol-2-yl SO₂Me 6-521  tert-butyl Cl F SO₂Me 6-522  tert-butyl Me SO₂Me SO₂Me 6-523  tert-butyl Me SO₂Me CF₃ 6-524  tert-butyl Me NMe₂ SO₂Me 6-525  tert-butyl Me S(O)Me CF₃ 6-526  tert-butyl Me SMe CF₃ 6-527  tert-butyl Me SO₂CH₂CH₂OMe CF₃ 6-528  tert-butyl Me pyrazol-1-yl SO₂Me 6-529  tert-butyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-530  tert-butyl Me 1,2,3-triazol-1-yl SO₂Me 6-531  tert-butyl Me 1,2,3-triazol-2-yl SO₂Me 6-532  tert-butyl Me Cl SO₂Me 6-533  tert-butyl Me Me SO₂Me 6-534  tert-butyl Me Me SMe 6-535  tert-butyl Me SO₂Me Cl 6-536  tert-butyl Me NMe₂ SO₂Me 6-537  tert-butyl Me NH(CH₂)₂OMe SO₂Me 6-538  tert-butyl CF₃ F SO₂CH₃ 6-539  tert-butyl CF₃ SMe SO₂CH₃ 6-540  tert-butyl CF₃ SEt SO₂CH₃ 6-541  tert-butyl CF₃ S(O)Et SO₂CH₃ 6-542  tert-butyl CF₃ SO₂CH₃ SO₂CH₃ 6-543  tert-butyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-544  tert-butyl CF₃ OCH₂(CO)NMe₂ SO₂Me 6-545  tert-butyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-546  tert-butyl SMe SMe F 6-547  tert-butyl SMe SEt F 6-548  tert-butyl SO₂CH₃ F Cl 6-549  tert-butyl F S(O)Me CF₃ 6-550  tert-butyl F SMe CF₃ 6-551  furan-2-yl NO₂ H SO₂Me 6-552  furan-2-yl Cl H SO₂Me 6-553  furan-2-yl SO₂Me H CF₃ 6-554  furan-2-yl NO₂ H OMe 6-555  furan-2-yl NO₂ H Br 6-556  furan-2-yl NO₂ H CF₃ 6-557  furan-2-yl NO₂ H NO₂ 6-558  furan-2-yl NO₂ H Cl 6-559  furan-2-yl NO₂ H Me 6-560  furan-2-yl NO₂ H F 6-561  furan-2-yl OMe H SO₂Me 6-562  furan-2-yl CF₃ H NO₂ 6-563  furan-2-yl CH₂SO₂Me H Br 6-564  furan-2-yl Cl CH₂OCH₂CF₃ SO₂Me 6-565  furan-2-yl Cl CH₂OCH₂CF₃ SMe 6-566  furan-2-yl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-567  furan-2-yl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-568  furan-2-yl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-569  furan-2-yl Cl SMe Cl 6-570  furan-2-yl Cl SMe SO₂Me 6-571  furan-2-yl Cl Me SO₂Et 6-572  furan-2-yl Cl O(CH₂)₂OMe Cl 6-573  furan-2-yl Cl OCH₂-cyclopropyl Cl 6-574  furan-2-yl Cl OMe Cl 6-575  furan-2-yl Cl NHAc Cl 6-576  furan-2-yl Cl OCH₂C(O)NMe₂ Cl 6-577  furan-2-yl Cl Cl SO₂Me 6-578  furan-2-yl Cl pyrazol-1-yl SO₂Me 6-579  furan-2-yl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-580  furan-2-yl Cl 1,2,3-triazol-1-yl SO₂Me 6-581  furan-2-yl Cl 1,2,3-triazol-2-yl SO₂Me 6-582  furan-2-yl Cl F SO₂Me 6-583  furan-2-yl Me SO₂Me SO₂Me 6-584  furan-2-yl Me SO₂Me CF₃ 6-585  furan-2-yl Me NMe₂ SO₂Me 6-586  furan-2-yl Me S(O)Me CF₃ 6-587  furan-2-yl Me SMe CF₃ 6-588  furan-2-yl Me SO₂CH₂CH₂OMe CF₃ 6-589  furan-2-yl Me pyrazol-1-yl SO₂Me 6-590  furan-2-yl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-591  furan-2-yl Me 1,2,3-triazol-1-yl SO₂Me 6-592  furan-2-yl Me 1,2,3-triazol-2-yl SO₂Me 6-593  furan-2-yl Me Cl SO₂Me 6-594  furan-2-yl Me Me SO₂Me 6-595  furan-2-yl Me Me SMe 6-596  furan-2-yl Me SO₂Me Cl 6-597  furan-2-yl Me NMe₂ SO₂Me 6-598  furan-2-yl Me NH(CH₂)₂OMe SO₂Me 6-599  furan-2-yl CF₃ F SO₂CH₃ 6-600  furan-2-yl CF₃ SMe SO₂CH₃ 6-601  furan-2-yl CF₃ SEt SO₂CH₃ 6-602  furan-2-yl CF₃ S(O)Et SO₂CH₃ 6-603  furan-2-yl CF₃ SO₂CH₃ SO₂CH₃ 6-604  furan-2-yl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-605  furan-2-yl CF₃ OCH₂(CO)NMe₂ SO₂Me 6-606  furan-2-yl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-607  furan-2-yl SMe SMe F 6-608  furan-2-yl SMe SEt F 6-609  furan-2-yl SO₂CH₃ F Cl 6-610  furan-2-yl F S(O)Me CF₃ 6-611  furan-2-yl F SMe CF₃ 6-612  isopropyl NO₂ H SO₂Me 6-613  isopropyl Cl H SO₂Me 6-614  isopropyl SO₂Me H CF₃ 6-615  isopropyl NO₂ H OMe 6-616  isopropyl NO₂ H Br 6-617  isopropyl NO₂ H CF₃ 6-618  isopropyl NO₂ H NO₂ 6-619  isopropyl NO₂ H Cl 6-620  isopropyl NO₂ H Me 6-621  isopropyl NO₂ H F 6-622  isopropyl OMe H SO₂Me 6-623  isopropyl CF₃ H NO₂ 6-624  isopropyl CH₂SO₂Me H Br 6-625  isopropyl Cl CH₂OCH₂CF₃ SO₂Me 6-626  isopropyl Cl CH₂OCH₂CF₃ SMe 6-627  isopropyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-628  isopropyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-629  isopropyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-630  isopropyl Cl SMe Cl 6-631  isopropyl Cl SMe SO₂Me 6-632  isopropyl Cl Me SO₂Et 6-633  isopropyl Cl O(CH₂)₂OMe Cl 6-634  isopropyl Cl OCH₂-cyclopropyl Cl 6-635  isopropyl Cl OMe Cl 6-636  isopropyl Cl NHAc Cl 6-637  isopropyl Cl OCH₂C(O)NMe₂ Cl 6-638  isopropyl Cl Cl SO₂Me 6-639  isopropyl Cl pyrazol-1-yl SO₂Me 6-640  isopropyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-641  isopropyl Cl 1,2,3-triazol-1-yl SO₂Me 6-642  isopropyl Cl 1,2,3-triazol-2-yl SO₂Me 6-643  isopropyl Cl F SO₂Me 6-644  isopropyl Me SO₂Me SO₂Me 6-645  isopropyl Me SO₂Me CF₃ 6-646  isopropyl Me NMe₂ SO₂Me 6-647  isopropyl Me S(O)Me CF₃ 6-648  isopropyl Me SMe CF₃ 6-649  isopropyl Me SO₂CH₂CH₂OMe CF₃ 6-650  isopropyl Me pyrazol-1-yl SO₂Me 6-651  isopropyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-652  isopropyl Me 1,2,3-triazol-1-yl SO₂Me 6-653  isopropyl Me 1,2,3-triazol-2-yl SO₂Me 6-654  isopropyl Me Cl SO₂Me 6-655  isopropyl Me Me SO₂Me 6-656  isopropyl Me F Cl 6-657  isopropyl Me SO₂Me Cl 6-658  isopropyl Me NMe₂ SO₂Me 6-659  isopropyl Me NH(CH₂)₂OMe SO₂Me 6-660  isopropyl CF₃ F SO₂CH₃ 6-661  isopropyl CF₃ SMe SO₂CH₃ 6-662  isopropyl CF₃ SEt SO₂CH₃ 6-663  isopropyl CF₃ S(O)Et SO₂CH₃ 6-664  isopropyl CF₃ SO₂CH₃ SO₂CH₃ 6-665  isopropyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-666  isopropyl CF₃ OCH₂(CO)NMe₂ SO₂Me 6-667  isopropyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-668  isopropyl SMe SMe F 6-669  isopropyl SMe SEt F 6-670  isopropyl SO₂CH₃ F Cl 6-671  isopropyl F S(O)Me CF₃ 6-672  isopropyl F SMe CF₃ 6-673  CH₂CH₂OMe NO₂ H SO₂Me 6-674  CH₂CH₂OMe Cl H SO₂Me 6-675  CH₂CH₂OMe SO₂Me H CF₃ 6-676  CH₂CH₂OMe NO₂ H OMe 6-677  CH₂CH₂OMe NO₂ H Br 6-678  CH₂CH₂OMe NO₂ H CF₃ 6-679  CH₂CH₂OMe NO₂ H NO₂ 6-680  CH₂CH₂OMe NO₂ H Cl 6-681  CH₂CH₂OMe NO₂ H Me 6-682  CH₂CH₂OMe NO₂ H F 6-683  CH₂CH₂OMe OMe H SO₂Me 6-684  CH₂CH₂OMe CF₃ H NO₂ 6-685  CH₂CH₂OMe CH₂SO₂Me H Br 6-686  CH₂CH₂OMe Cl CH₂OCH₂CF₃ SO₂Me 6-687  CH₂CH₂OMe Cl CH₂OCH₂CF₃ SMe 6-688  CH₂CH₂OMe Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-689  CH₂CH₂OMe Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-690  CH₂CH₂OMe Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-691  CH₂CH₂OMe Cl SMe Cl 6-692  CH₂CH₂OMe Cl SMe SO₂Me 6-693  CH₂CH₂OMe Cl Me SO₂Et 6-694  CH₂CH₂OMe Cl O(CH₂)₂OMe Cl 6-695  CH₂CH₂OMe Cl OCH₂-cyclopropyl Cl 6-696  CH₂CH₂OMe Cl OMe Cl 6-697  CH₂CH₂OMe Cl NHAc Cl 6-698  CH₂CH₂OMe Cl OCH₂C(O)NMe₂ Cl 6-699  CH₂CH₂OMe Cl Cl SO₂Me 6-700  CH₂CH₂OMe Cl pyrazol-1-yl SO₂Me 6-701  CH₂CH₂OMe Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-702  CH₂CH₂OMe Cl 1,2,3-triazol-1-yl SO₂Me 6-703  CH₂CH₂OMe Cl 1,2,3-triazol-2-yl SO₂Me 6-704  CH₂CH₂OMe Cl F SO₂Me 6-705  CH₂CH₂OMe Me SO₂Me SO₂Me 6-706  CH₂CH₂OMe Me SO₂Me CF₃ 6-707  CH₂CH₂OMe Me NMe₂ SO₂Me 6-708  CH₂CH₂OMe Me S(O)Me CF₃ 6-709  CH₂CH₂OMe Me SMe CF₃ 6-710  CH₂CH₂OMe Me SO₂CH₂CH₂OMe CF₃ 6-711  CH₂CH₂OMe Me pyrazol-1-yl SO₂Me 6-712  CH₂CH₂OMe Me 4-methoxy- SO₂Me pyrazol-1-yl 6-713  CH₂CH₂OMe Me 1,2,3-triazol-1-yl SO₂Me 6-714  CH₂CH₂OMe Me 1,2,3-triazol-2-yl SO₂Me 6-715  CH₂CH₂OMe Me Cl SO₂Me 6-716  CH₂CH₂OMe Me Me SO₂Me 6-717  CH₂CH₂OMe Me Me SMe 6-718  CH₂CH₂OMe Me SO₂Me Cl 6-719  CH₂CH₂OMe Me NMe₂ SO₂Me 6-720  CH₂CH₂OMe Me NH(CH₂)₂OMe SO₂Me 6-721  CH₂CH₂OMe CF₃ F SO₂CH₃ 6-722  CH₂CH₂OMe CF₃ SMe SO₂CH₃ 6-723  CH₂CH₂OMe CF₃ SEt SO₂CH₃ 6-724  CH₂CH₂OMe CF₃ S(O)Et SO₂CH₃ 6-725  CH₂CH₂OMe CF₃ SO₂CH₃ SO₂CH₃ 6-726  CH₂CH₂OMe CF₃ OCH₂CH₂OMe SO₂CH₃ 6-727  CH₂CH₂OMe CF₃ OCH₂(CO)NMe₂ SO2Me 6-728  CH₂CH₂OMe CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-729  CH₂CH₂OMe SMe SMe F 6-730  CH₂CH₂OMe SMe SEt F 6-731  CH₂CH₂OMe SO₂CH₃ F Cl 6-732  CH₂CH₂OMe F S(O)Me CF₃ 6-733  CH₂CH₂OMe F SMe CF₃ 6-734  CH₂CF₃ NO₂ H SO₂Me 6-735  CH₂CF₃ Cl H SO₂Me 6-736  CH₂CF₃ SO₂Me H CF₃ 6-737  CH₂CF₃ NO₂ H OMe 6-738  CH₂CF₃ NO₂ H Br 6-739  CH₂CF₃ NO₂ H CF₃ 6-740  CH₂CF₃ NO₂ H NO₂ 6-741  CH₂CF₃ NO₂ H Cl 6-742  CH₂CF₃ NO₂ H Me 6-743  CH₂CF₃ NO₂ H F 6-744  CH₂CF₃ OMe H SO₂Me 6-745  CH₂CF₃ CF₃ H NO₂ 6-746  CH₂CF₃ CH₂SO₂Me H Br 6-747  CH₂CF₃ Cl CH₂OCH₂CF₃ SO₂Me 6-748  CH₂CF₃ Cl CH₂OCH₂CF₃ SMe 6-749  CH₂CF₃ Cl 5-cyanomethyl-4,5- SO₂Et dihydro-1,2-oxazol- 3-yl 6-750  CH₂CF₃ Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-751  CH₂CF₃ Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-752  CH₂CF₃ Cl SMe Cl 6-753  CH₂CF₃ Cl SMe SO₂Me 6-754  CH₂CF₃ Cl Me SO₂Et 6-755  CH₂CF₃ Cl O(CH₂)₂OMe Cl 6-756  CH₂CF₃ Cl OCH₂-cyclopropyl Cl 6-757  CH₂CF₃ Cl OMe Cl 6-758  CH₂CF₃ Cl NHAc Cl 6-759  CH₂CF₃ Cl OCH₂C(O)NMe₂ Cl 6-760  CH₂CF₃ Cl Cl SO₂Me 6-761  CH₂CF₃ Cl pyrazol-1-yl SO₂Me 6-762  CH₂CF₃ Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-763  CH₂CF₃ Cl 1 ,2,3-triazol-1-yl SO₂Me 6-764  CH₂CF₃ Cl 1,2,3-triazol-2-yl SO₂Me 6-765  CH₂CF₃ Cl F SO₂Me 6-766  CH₂CF₃ Me SO₂Me SO₂Me 6-767  CH₂CF₃ Me SO₂Me CF₃ 6-768  CH₂CF₃ Me NMe₂ SO₂Me 6-769  CH₂CF₃ Me S(O)Me CF₃ 6-770  CH₂CF₃ Me SMe CF₃ 6-771  CH₂CF₃ Me SO₂CH₂CH₂OMe CF₃ 6-772  CH₂CF₃ Me pyrazol-1-yl SO₂Me 6-773  CH₂CF₃ Me 4-methoxy- SO₂Me pyrazol-1-yl 6-774  CH₂CF₃ Me 1,2,3-triazol-1-yl SO₂Me 6-775  CH₂CF₃ Me 1,2,3-triazol-2-yl SO₂Me 6-776  CH₂CF₃ Me Cl SO₂Me 6-777  CH₂CF₃ Me Me SO₂Me 6-778  CH₂CF₃ Me Me SMe 6-779  CH₂CF₃ Me SO₂Me Cl 6-780  CH₂CF₃ Me NMe₂ SO₂Me 6-781  CH₂CF₃ Me NH(CH₂)₂OMe SO₂Me 6-782  CH₂CF₃ CF₃ F SO₂CH₃ 6-783  CH₂CF₃ CF₃ SMe SO₂CH₃ 6-784  CH₂CF₃ CF₃ SEt SO₂CH₃ 6-785  CH₂CF₃ CF₃ S(O)Et SO₂CH₃ 6-786  CH₂CF₃ CF₃ SO₂CH₃ SO₂CH₃ 6-787  CH₂CF₃ CF₃ OCH₂CH₂OMe SO₂CH₃ 6-788  CH₂CF₃ CF₃ OCH₂(CO)NMe₂ SO₂Me 6-789  CH₂CF₃ CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-790  CH₂CF₃ SMe SMe F 6-791  CH₂CF₃ SMe SEt F 6-792  CH₂CF₃ SO₂CH₃ F Cl 6-793  CH₂CF₃ F S(O)Me CF₃ 6-794  CH₂CF₃ F SMe CF₃ 6-795  tetrahydro- NO₂ H SO₂Me furan-2-yl 6-796  tetrahydro- Cl H SO₂Me furan-2-yl 6-797  tetrahydro- SO₂Me H CF₃ furan-2-yl 6-798  tetrahydro- NO₂ H OMe furan-2-yl 6-799  tetrahydro- NO₂ H Br furan-2-yl 6-800  tetrahydro- NO₂ H CF₃ furan-2-yl 6-801  tetrahydro- NO₂ H NO₂ furan-2-yl 6-802  tetrahydro- NO₂ H Cl furan-2-yl 6-803  tetrahydro- NO₂ H Me furan-2-yl 6-804  tetrahydro- NO₂ H F furan-2-yl 6-805  tetrahydro- OMe H SO₂Me furan-2-yl 6-806  tetrahydro- CF₃ H NO₂ furan-2-yl 6-807  tetrahydro- CH₂SO₂Me H Br furan-2-yl 6-808  tetrahydro- Cl CH₂OCH₂CF₃ SO₂Me furan-2-yl 6-809  tetrahydro- Cl CH₂OCH₂CF₃ SMe furan-2-yl 6-810  tetrahydro- Cl 5-cyanomethyl- SO₂Et furan-2-yl 4,5-dihydro- 1,2-oxazol-3-yl 6-811  tetrahydro- Cl 4,5-dihydro-1,2- SO₂Et furan-2-yl oxazol-3-yl 6-812  tetrahydro- Cl CH₂OCH₂- SO₂Me furan-2-yl tetrahydrofuran-2-yl 6-813  tetrahydro- Cl SMe Cl furan-2-yl 6-814  tetrahydro- Cl SMe SO₂Me furan-2-yl 6-815  tetrahydro- Cl Me SO₂Et furan-2-yl 6-816  tetrahydro- Cl O(CH₂)₂OMe Cl furan-2-yl 6-817  tetrahydro- Cl OCH₂-cyclopropyl Cl furan-2-yl 6-818  tetrahydro- Cl OMe Cl furan-2-yl 6-819  tetrahydro- Cl NHAc Cl furan-2-yl 6-820  tetrahydro- Cl OCH₂C(O)NMe₂ Cl furan-2-yl 6-821  tetrahydro- Cl Cl SO₂Me furan-2-yl 6-822  tetrahydro- Cl pyrazol-1-yl SO₂Me furan-2-yl 6-823  tetrahydro- Cl 4-methoxy- SO₂Me furan-2-yl pyrazol-1-yl 6-824  tetrahydro- Cl 1,2,3-triazol-1-yl SO₂Me furan-2-yl 6-825  tetrahydro- Cl 1,2,3-triazol-2-yl SO₂Me furan-2-yl 6-826  tetrahydro- Cl F SO₂Me furan-2-yl 6-827  tetrahydro- Me SO₂Me SO₂Me furan-2-yl 6-828  tetrahydro- Me SO₂Me CF₃ furan-2-yl 6-829  tetrahydro- Me NMe₂ SO₂Me furan-2-yl 6-830  tetrahydro- Me S(O)Me CF₃ furan-2-yl 6-831  tetrahydro- Me SMe CF₃ furan-2-yl 6-832  tetrahydro- Me SO₂CH₂CH₂OMe CF₃ furan-2-yl 6-833  tetrahydro- Me pyrazol-1-yl SO₂Me furan-2-yl 6-834  tetrahydro- Me 4-methoxy- SO₂Me furan-2-yl pyrazol-1-yl 6-835  tetrahydro- Me 1,2,3-triazol-1-yl SO₂Me furan-2-yl 6-836  tetrahydro- Me 1,2,3-triazol-2-yl SO₂Me furan-2-yl 6-837  tetrahydro- Me Cl SO₂Me furan-2-yl 6-838  tetrahydro- Me Me SO₂Me furan-2-yl 6-839  tetrahydro- Me Me SMe furan-2-yl 6-840  tetrahydro- Me SO₂Me Cl furan-2-yl 6-841  tetrahydro- Me NMe₂ SO₂Me furan-2-yl 6-842  tetrahydro- Me NH(CH₂)₂OMe SO₂Me furan-2-yl 6-843  tetrahydro- CF₃ F SO₂CH₃ furan-2-yl 6-844  tetrahydro- CF₃ SMe SO₂CH₃ furan-2-yl 6-845  tetrahydro- CF₃ SEt SO₂CH₃ furan-2-yl 6-846  tetrahydro- CF₃ S(O)Et SO₂CH₃ furan-2-yl 6-847  tetrahydro- CF₃ SO₂CH₃ SO₂CH₃ furan-2-yl 6-848  tetrahydro- CF₃ OCH₂CH₂OMe SO₂CH₃ furan-2-yl 6-849  tetrahydro- CF₃ OCH₂(CO)NMe₂ SO2Me furan-2-yl 6-850  tetrahydro- CF₃ CH₂O- SO₂Et furan-2-yl tetrahydrofuran-2-yl 6-851  tetrahydro- SMe SMe F furan-2-yl 6-852  tetrahydro- SMe SEt F furan-2-yl 6-853  tetrahydro- SO₂CH₃ F Cl furan-2-yl 6-854  tetrahydro- F S(O)Me CF₃ furan-2-yl 6-855  tetrahydro- F SMe CF₃ furan-2-yl 6-856  n-Pr NO₂ H SO₂Me 6-857  n-Pr Cl H SO₂Me 6-858  n-Pr SO₂Me H CF₃ 6-859  n-Pr NO₂ H OMe 6-860  n-Pr NO₂ H Br 6-861  n-Pr NO₂ H Cl 6-862  n-Pr NO₂ H CF₃ 6-863  n-Pr NO₂ H NO₂ 6-864  n-Pr NO₂ H Me 6-865  n-Pr NO₂ H F 6-866  n-Pr OMe H SO₂Me 6-867  n-Pr CF₃ H NO₂ 6-868  n-Pr CH₂SO₂Me H Br 6-869  n-Pr Cl CH₂OCH₂CF₃ SO₂Me 6-870  n-Pr Cl CH₂OCH₂CF₃ SMe 6-871  n-Pr Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-872  n-Pr Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-873  n-Pr Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-874  n-Pr Cl SMe Cl 6-875  n-Pr Cl SMe SO₂Me 6-876  n-Pr Cl Me SO₂Et 6-877  n-Pr Cl O(CH₂)₂OMe Cl 6-878  n-Pr Cl OCH₂-cyclopropyl Cl 6-879  n-Pr Cl OMe Cl 6-880  n-Pr Cl NHAc Cl 6-881  n-Pr Cl OCH₂C(O)NMe₂ Cl 6-882  n-Pr Cl Cl SO₂Me 6-883  n-Pr Cl pyrazol-1-yl SO₂Me 6-884  n-Pr Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-885  n-Pr Cl 1,2,3-triazol-1-yl SO₂Me 6-886  n-Pr Cl 1,2,3-triazol-2-yl SO₂Me 6-887  n-Pr Cl F SO₂Me 6-888  n-Pr Me SO₂Me SO₂Me 6-889  n-Pr Me SO₂Me CF₃ 6-890  n-Pr Me NMe₂ SO₂Me 6-891  n-Pr Me S(O)Me CF₃ 6-892  n-Pr Me SMe CF₃ 6-893  n-Pr Me SO₂CH₂CH₂OMe CF₃ 6-894  n-Pr Me pyrazol-1-yl SO₂Me 6-895  n-Pr Me 4-methoxy- SO₂Me pyrazol-1-yl 6-896  n-Pr Me 1,2,3-triazol-1-yl SO₂Me 6-897  n-Pr Me 1,2,3-triazol-2-yl SO₂Me 6-898  n-Pr Me Cl SO₂Me 6-899  n-Pr Me Me SO₂Me 6-900  n-Pr Me Me SMe 6-901  n-Pr Me SO₂Me Cl 6-902  n-Pr Me NMe₂ SO₂Me 6-903  n-Pr Me NH(CH₂)₂OMe SO₂Me 6-904  n-Pr CF₃ F SO₂CH₃ 6-905  n-Pr CF₃ SMe SO₂CH₃ 6-906  n-Pr CF₃ SEt SO₂CH₃ 6-907  n-Pr CF₃ S(O)Et SO₂CH₃ 6-908  n-Pr CF₃ SO₂CH₃ SO₂CH₃ 6-909  n-Pr CF₃ OCH₂CH₂OMe SO₂CH₃ 6-910  n-Pr CF₃ OCH₂(CO)NMe₂ SO2Me 6-911  n-Pr CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-912  n-Pr SMe SMe F 6-913  n-Pr SMe SEt F 6-914  n-Pr SO₂CH₃ F Cl 6-915  n-Pr F S(O)Me CF₃ 6-916  n-Pr F SMe CF₃ 6-917  CH₂OEt NO₂ H SO₂Me 6-918  CH₂OEt Cl H SO₂Me 6-919  CH₂OEt SO₂Me H CF₃ 6-920  CH₂OEt NO₂ H OMe 6-921  CH₂OEt NO₂ H Br 6-922  CH₂OEt NO₂ H CF₃ 6-923  CH₂OEt NO₂ H NO₂ 6-924  CH₂OEt NO₂ H Cl 6-925  CH₂OEt NO₂ H Me 6-926  CH₂OEt NO₂ H F 6-927  CH₂OEt OMe H SO₂Me 6-928  CH₂OEt CF₃ H NO₂ 6-929  CH₂OEt CH₂SO₂Me H Br 6-930  CH₂OEt Cl CH₂OCH₂CF₃ SO₂Me 6-931  CH₂OEt Cl CH₂OCH₂CF₃ SMe 6-932  CH₂OEt Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-933  CH₂OEt Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-934  CH₂OEt Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-935  CH₂OEt Cl SMe Cl 6-936  CH₂OEt Cl SMe SO₂Me 6-937  CH₂OEt Cl Me SO₂Et 6-938  CH₂OEt Cl O(CH₂)₂OMe Cl 6-939  CH₂OEt Cl OCH₂-cyclopropyl Cl 6-940  CH₂OEt Cl OMe Cl 6-941  CH₂OEt Cl NHAc Cl 6-942  CH₂OEt Cl OCH₂C(O)NMe₂ Cl 6-943  CH₂OEt Cl Cl SO₂Me 6-944  CH₂OEt Cl pyrazol-1-yl SO₂Me 6-945  CH₂OEt Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-946  CH₂OEt Cl 1,2,3-triazol-1-yl SO₂Me 6-947  CH₂OEt Cl 1,2,3-triazol-2-yl SO₂Me 6-948  CH₂OEt Cl F SO₂Me 6-949  CH₂OEt Me SO₂Me SO₂Me 6-950  CH₂OEt Me SO₂Me CF₃ 6-951  CH₂OEt Me NMe₂ SO₂Me 6-952  CH₂OEt Me S(O)Me CF₃ 6-953  CH₂OEt Me SMe CF₃ 6-954  CH₂OEt Me SO₂CH₂CH₂OMe CF₃ 6-955  CH₂OEt Me pyrazol-1-yl SO₂Me 6-956  CH₂OEt Me 4-methoxy- SO₂Me pyrazol-1-yl 6-957  CH₂OEt Me 1,2,3-triazol-1-yl SO₂Me 6-958  CH₂OEt Me 1,2,3-triazol-2-yl SO₂Me 6-959  CH₂OEt Me Cl SO₂Me 6-960  CH₂OEt Me Me SO₂Me 6-961  CH₂OEt Me Me SMe 6-962  CH₂OEt Me SO₂Me Cl 6-963  CH₂OEt Me NMe₂ SO₂Me 6-964  CH₂OEt Me NH(CH₂)₂OMe SO₂Me 6-965  CH₂OEt CF₃ F SO₂CH₃ 6-966  CH₂OEt CF₃ SMe SO₂CH₃ 6-967  CH₂OEt CF₃ SEt SO₂CH₃ 6-968  CH₂OEt CF₃ S(O)Et SO₂CH₃ 6-969  CH₂OEt CF₃ SO₂CH₃ SO₂CH₃ 6-970  CH₂OEt CF₃ OCH₂CH₂OMe SO₂CH₃ 6-971  CH₂OEt CF₃ OCH₂(CO)NMe₂ SO2Me 6-972  CH₂OEt CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-973  CH₂OEt SMe SMe F 6-974  CH₂OEt SMe SEt F 6-975  CH₂OEt SO₂CH₃ F Cl 6-976  CH₂OEt F S(O)Me CF₃ 6-977  CH₂OEt F SMe CF₃ 6-978  cyclobutyl NO₂ H SO₂Me 6-979  cyclobutyl Cl H SO₂Me 6-980  cyclobutyl SO₂Me H CF₃ 6-981  cyclobutyl NO₂ H OMe 6-982  cyclobutyl NO₂ H Br 6-983  cyclobutyl SMe H CF₃ 6-984  cyclobutyl NO₂ H NO₂ 6-985  cyclobutyl NO₂ H Cl 6-986  cyclobutyl NO₂ H Me 6-987  cyclobutyl NO₂ H F 6-988  cyclobutyl OMe H SO₂Me 6-989  cyclobutyl CF₃ H NO₂ 6-990  cyclobutyl CH₂SO₂Me H Br 6-991  cyclobutyl Cl CH₂OCH₂CF₃ SO₂Me 6-992  cyclobutyl Cl CH₂OCH₂CF₃ SMe 6-993  cyclobutyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-994  cyclobutyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-995  cyclobutyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-996  cyclobutyl Cl SMe Cl 6-997  cyclobutyl Cl SMe SO₂Me 6-998  cyclobutyl Cl Me SO₂Et 6-999  cyclobutyl Cl O(CH₂)₂OMe Cl 6-1000 cyclobutyl Cl OCH₂-cyclopropyl Cl 6-1001 cyclobutyl Cl OMe Cl 6-1002 cyclobutyl Cl NHAc Cl 6-1003 cyclobutyl Cl OCH₂C(O)NMe₂ Cl 6-1004 cyclobutyl Cl Cl SO₂Me 6-1005 cyclobutyl Cl pyrazol-1-yl SO₂Me 6-1006 cyclobutyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1007 cyclobutyl Cl 1,2,3-triazol-1-yl SO₂Me 6-1008 cyclobutyl Cl 1,2,3-triazol-2-yl SO₂Me 6-1009 cyclobutyl Cl F SO₂Me 6-1010 cyclobutyl Me SO₂Me SO₂Me 6-1011 cyclobutyl Me SO₂Me CF₃ 6-1012 cyclobutyl Me NMe₂ SO₂Me 6-1013 cyclobutyl Me S(O)Me CF₃ 6-1014 cyclobutyl Me SMe CF₃ 6-1015 cyclobutyl Me SO₂CH₂CH₂OMe CF₃ 6-1016 cyclobutyl Me pyrazol-1-yl SO₂Me 6-1017 cyclobutyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1018 cyclobutyl Me 1,2,3-triazol-1-yl SO₂Me 6-1019 cyclobutyl Me 1,2,3-triazol-2-yl SO₂Me 6-1020 cyclobutyl Me Cl SO₂Me 6-1021 cyclobutyl Me Me SO₂Me 6-1022 cyclobutyl Me Me SMe 6-1023 cyclobutyl Me SO₂Me Cl 6-1024 cyclobutyl Me NMe₂ SO₂Me 6-1025 cyclobutyl Me NH(CH₂)₂OMe SO₂Me 6-1026 cyclobutyl CF₃ F SO₂CH₃ 6-1027 cyclobutyl CF₃ SMe SO₂CH₃ 6-1028 cyclobutyl CF₃ SEt SO₂CH₃ 6-1029 cyclobutyl CF₃ S(O)Et SO₂CH₃ 6-1030 cyclobutyl CF₃ SO₂CH₃ SO₂CH₃ 6-1031 cyclobutyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1032 cyclobutyl CF₃ OCH₂(CO)NMe₂ SO₂Me 6-1033 cyclobutyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1034 cyclobutyl SMe SMe F 6-1035 cyclobutyl SMe SEt F 6-1036 cyclobutyl SO₂CH₃ F Cl 6-1037 cyclobutyl F S(O)Me CF₃ 6-1038 cyclobutyl F SMe CF₃ 6-1039 cyclopentyl NO₂ H SO₂Me 6-1040 cyclopentyl Cl H SO₂Me 6-1041 cyclopentyl SO₂Me H CF₃ 6-1042 cyclopentyl NO₂ H OMe 6-1043 cyclopentyl NO₂ H Br 6-1044 cyclopentyl SMe H CF₃ 6-1045 cyclopentyl NO₂ H NO₂ 6-1046 cyclopentyl NO₂ H Cl 6-1047 cyclopentyl NO₂ H Me 6-1048 cyclopentyl NO₂ H F 6-1049 cyclopentyl OMe H SO₂Me 6-1050 cyclopentyl CF₃ H NO₂ 6-1051 cyclopentyl CH₂SO₂Me H Br 6-1052 cyclopentyl Cl CH₂OCH₂CF₃ SO₂Me 6-1053 cyclopentyl Cl CH₂OCH₂CF₃ SMe 6-1054 cyclopentyl Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-1055 cyclopentyl Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-1056 cyclopentyl Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1057 cyclopentyl Cl SMe Cl 6-1058 cyclopentyl Cl SMe SO₂Me 6-1059 cyclopentyl Cl Me SO₂Et 6-1060 cyclopentyl Cl O(CH₂)₂OMe Cl 6-1061 cyclopentyl Cl OCH₂-cyclopropyl Cl 6-1062 cyclopentyl Cl OMe Cl 6-1063 cyclopentyl Cl NHAc Cl 6-1064 cyclopentyl Cl OCH₂C(O)NMe₂ Cl 6-1065 cyclopentyl Cl Cl SO₂Me 6-1066 cyclopentyl Cl pyrazol-1-yl SO₂Me 6-1067 cyclopentyl Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1068 cyclopentyl Cl 1,2,3-triazol-1-yl SO₂Me 6-1069 cyclopentyl Cl 1,2,3-triazol-2-yl SO₂Me 6-1070 cyclopentyl Cl F SO₂Me 6-1071 cyclopentyl Me SO₂Me SO₂Me 6-1072 cyclopentyl Me SO₂Me CF₃ 6-1073 cyclopentyl Me NMe₂ SO₂Me 6-1074 cyclopentyl Me S(O)Me CF₃ 6-1075 cyclopentyl Me SMe CF₃ 6-1076 cyclopentyl Me SO₂CH₂CH₂OMe CF₃ 6-1077 cyclopentyl Me pyrazol-1-yl SO₂Me 6-1078 cyclopentyl Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1079 cyclopentyl Me 1,2,3-triazol-1-yl SO₂Me 6-1080 cyclopentyl Me 1,2,3-triazol-2-yl SO₂Me 6-1081 cyclopentyl Me Cl SO₂Me 6-1082 cyclopentyl Me Me SO₂Me 6-1083 cyclopentyl Me Me SMe 6-1084 cyclopentyl Me SO₂Me Cl 6-1085 cyclopentyl Me NMe₂ SO₂Me 6-1086 cyclopentyl Me NH(CH₂)₂OMe SO₂Me 6-1087 cyclopentyl CF₃ F SO₂CH₃ 6-1088 cyclopentyl CF₃ SMe SO₂CH₃ 6-1089 cyclopentyl CF₃ SEt SO₂CH₃ 6-1090 cyclopentyl CF₃ S(O)Et SO₂CH₃ 6-1091 cyclopentyl CF₃ SO₂CH₃ SO₂CH₃ 6-1092 cyclopentyl CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1093 cyclopentyl CF₃ OCH₂(CO)NMe₂ SO2Me 6-1094 cyclopentyl CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1095 cyclopentyl SMe SMe F 6-1096 cyclopentyl SMe SEt F 6-1097 cyclopentyl SO₂CH₃ F Cl 6-1098 cyclopentyl F S(O)Me CF₃ 6-1099 cyclopentyl F SMe CF₃ 6-1100 Me₂N NO₂ H SO₂Me 6-1101 Me₂N Cl H SO₂Me 6-1102 Me₂N SO₂Me H CF₃ 6-1103 Me₂N NO₂ H OMe 6-1104 Me₂N NO₂ H Br 6-1105 Me₂N NO₂ H CF₃ 6-1106 Me₂N NO₂ H NO₂ 6-1107 Me₂N NO₂ H Cl 6-1108 Me₂N NO₂ H Me 6-1109 Me₂N NO₂ H F 6-1110 Me₂N OMe H SO₂Me 6-1111 Me₂N CF₃ H NO₂ 6-1112 Me₂N CH₂SO₂Me H Br 6-1113 Me₂N Cl CH₂OCH₂CF₃ SO₂Me 6-1114 Me₂N Cl CH₂OCH₂CF₃ SMe 6-1115 Me₂N Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-1116 Me₂N Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-1117 Me₂N Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1118 Me₂N Cl SMe Cl 6-1119 Me₂N Cl SMe SO₂Me 6-1120 Me₂N Cl Me SO₂Et 6-1121 Me₂N Cl O(CH₂)₂OMe Cl 6-1122 Me₂N Cl OCH₂-cyclopropyl Cl 6-1123 Me₂N Cl OMe Cl 6-1124 Me₂N Cl NHAc Cl 6-1125 Me₂N Cl OCH₂C(O)NMe₂ Cl 6-1126 Me₂N Cl Cl SO₂Me 6-1127 Me₂N Cl pyrazol-1-yl SO₂Me 6-1128 Me₂N Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1129 Me₂N Cl 1,2,3-triazol-1-yl SO₂Me 6-1130 Me₂N Cl 1,2,3-triazol-2-yl SO₂Me 6-1131 Me₂N Cl F SO₂Me 6-1132 Me₂N Me SO₂Me SO₂Me 6-1133 Me₂N Me SO₂Me CF₃ 6-1134 Me₂N Me NMe₂ SO₂Me 6-1135 Me₂N Me S(O)Me CF₃ 6-1136 Me₂N Me SMe CF₃ 6-1137 Me₂N Me SO₂CH₂CH₂OMe CF₃ 6-1138 Me₂N Me pyrazol-1-yl SO₂Me 6-1139 Me₂N Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1140 Me₂N Me 1,2,3-triazol-1-yl SO₂Me 6-1141 Me₂N Me 1,2,3-triazol-2-yl SO₂Me 6-1142 Me₂N Me Cl SO₂Me 6-1143 Me₂N Me Me SO₂Me 6-1144 Me₂N Me Me SMe 6-1145 Me₂N Me SO₂Me Cl 6-1146 Me₂N Me NMe₂ SO₂Me 6-1147 Me₂N Me NH(CH₂)₂OMe SO₂Me 6-1148 Me₂N CF₃ F SO₂CH₃ 6-1149 Me₂N CF₃ SMe SO₂CH₃ 6-1150 Me₂N CF₃ SEt SO₂CH₃ 6-1151 Me₂N CF₃ S(O)Et SO₂CH₃ 6-1152 Me₂N CF₃ SO₂CH₃ SO₂CH₃ 6-1153 Me₂N CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1154 Me₂N CF₃ OCH₂(CO)NMe₂ SO2Me 6-1155 Me₂N CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1156 Me₂N SMe SMe F 6-1157 Me₂N SMe SEt F 6-1158 Me₂N SO₂CH₃ F Cl 6-1159 Me₂N F S(O)Me CF₃ 6-1160 Me₂N F SMe CF₃ 6-1161 Ph—NH NO₂ H SO₂Me 6-1162 Ph—NH Cl H SO₂Me 6-1163 Ph—NH SO₂Me H CF₃ 6-1164 Ph—NH NO₂ H OMe 6-1165 Ph—NH NO₂ H Br 6-1166 Ph—NH NO₂ H CF₃ 6-1167 Ph—NH NO₂ H NO₂ 6-1168 Ph—NH NO₂ H Cl 6-1169 Ph—NH NO₂ H Me 6-1170 Ph—NH NO₂ H F 6-1171 Ph—NH OMe H SO₂Me 6-1172 Ph—NH CF₃ H NO₂ 6-1173 Ph—NH CH₂SO₂Me H Br 6-1174 Ph—NH Cl CH₂OCH₂CF₃ SO₂Me 6-1175 Ph—NH Cl CH₂OCH₂CF₃ SMe 6-1176 Ph—NH Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-1177 Ph—NH Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-1178 Ph—NH Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1179 Ph—NH Cl SMe Cl 6-1180 Ph—NH Cl SMe SO₂Me 6-1181 Ph—NH Cl Me SO₂Et 6-1182 Ph—NH Cl O(CH₂)₂OMe Cl 6-1183 Ph—NH Cl OCH₂-cyclopropyl Cl 6-1184 Ph—NH Cl OMe Cl 6-1185 Ph—NH Cl NHAc Cl 6-1186 Ph—NH Cl OCH₂C(O)NMe₂ Cl 6-1187 Ph—NH Cl Cl SO₂Me 6-1188 Ph—NH Cl pyrazol-1-yl SO₂Me 6-1189 Ph—NH Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1190 Ph—NH Cl 1,2,3-triazol-1-yl SO₂Me 6-1191 Ph—NH Cl 1,2,3-triazol-2-yl SO₂Me 6-1192 Ph—NH Cl F SO₂Me 6-1193 Ph—NH Me SO₂Me SO₂Me 6-1194 Ph—NH Me SO₂Me CF₃ 6-1195 Ph—NH Me NMe₂ SO₂Me 6-1196 Ph—NH Me S(O)Me CF₃ 6-1197 Ph—NH Me SMe CF₃ 6-1198 Ph—NH Me SO₂CH₂CH₂OMe CF₃ 6-1199 Ph—NH Me pyrazol-1-yl SO₂Me 6-1200 Ph—NH Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1201 Ph—NH Me 1,2,3-triazol-1-yl SO₂Me 6-1202 Ph—NH Me 1,2,3-triazol-2-yl SO₂Me 6-1203 Ph—NH Me Cl SO₂Me 6-1204 Ph—NH Me Me SO₂Me 6-1205 Ph—NH Me Me SMe 6-1206 Ph—NH Me SO₂Me Cl 6-1207 Ph—NH Me NMe₂ SO₂Me 6-1208 Ph—NH Me NH(CH₂)₂OMe SO₂Me 6-1209 Ph—NH CF₃ F SO₂CH₃ 6-1210 Ph—NH CF₃ SMe SO₂CH₃ 6-1211 Ph—NH CF₃ SEt SO₂CH₃ 6-1212 Ph—NH CF₃ S(O)Et SO₂CH₃ 6-1213 Ph—NH CF₃ SO₂CH₃ SO₂CH₃ 6-1214 Ph—NH CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1215 Ph—NH CF₃ OCH₂(CO)NMe₂ SO2Me 6-1216 Ph—NH CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1217 Ph—NH SMe SMe F 6-1218 Ph—NH SMe SEt F 6-1219 Ph—NH SO₂CH₃ F Cl 6-1220 Ph—NH F S(O)Me CF₃ 6-1221 Ph—NH F SMe CF₃ 6-1222 morpholin- NO₂ H SO₂Me 1-yl 6-1223 morpholin- Cl H SO₂Me 1-yl 6-1224 morpholin- SO₂Me H CF₃ 1-yl 6-1225 morpholin- NO₂ H OMe 1-yl 6-1226 morpholin- NO₂ H Br 1-yl 6-1227 morpholin- NO₂ H CF₃ 1-yl 6-1228 morpholin- NO₂ H NO₂ 1-yl 6-1229 morpholin- NO₂ H Cl 1-yl 6-1230 morpholin- NO₂ H Me 1-yl 6-1231 morpholin- NO₂ H F 1-yl 6-1232 morpholin- OMe H SO₂Me 1-yl 6-1233 morpholin- CF₃ H NO₂ 1-yl 6-1234 morpholin- CH₂SO₂Me H Br 1-yl 6-1235 morpholin- Cl CH₂OCH₂CF₃ SO₂Me 1-yl 6-1236 morpholin- Cl CH₂OCH₂CF₃ SMe 1-yl 6-1237 morpholin- Cl 5-cyanomethyl- SO₂Et 1-yl 4,5-dihydro- 1,2-oxazol-3-yl 6-1238 morpholin- Cl 4,5-dihydro-1,2- SO₂Et 1-yl oxazol-3-yl 6-1239 morpholin- Cl CH₂OCH₂- SO₂Me 1-yl tetrahydrofuran-2-yl 6-1240 morpholin- Cl SMe Cl 1-yl 6-1241 morpholin- Cl SMe SO₂Me 1-yl 6-1242 morpholin- Cl Me SO₂Et 1-yl 6-1243 morpholin- Cl O(CH₂)₂OMe Cl 1-yl 6-1244 morpholin- Cl OCH₂-cyclopropyl Cl 1-yl 6-1245 morpholin- Cl OMe Cl 1-yl 6-1246 morpholin- Cl NHAc Cl 1-yl 6-1247 morpholin- Cl OCH₂C(O)NMe₂ Cl 1-yl 6-1248 morpholin- Cl Cl SO₂Me 1-yl 6-1249 morpholin- Cl pyrazol-1-yl SO₂Me 1-yl 6-1250 morpholin- Cl 4-methoxy- SO₂Me 1-yl pyrazol-1-yl 6-1251 morpholin- Cl 1,2,3-triazol-1-yl SO₂Me 1-yl 6-1252 morpholin- Cl 1,2,3-triazol-2-yl SO₂Me 1-yl 6-1253 morpholin- Cl F SO₂Me 1-yl 6-1254 morpholin- Me SO₂Me SO₂Me 1-yl 6-1255 morpholin- Me SO₂Me CF₃ 1-yl 6-1256 morpholin- Me NMe₂ SO₂Me 1-yl 6-1257 morpholin- Me S(O)Me CF₃ 1-yl 6-1258 morpholin- Me SMe CF₃ 1-yl 6-1259 morpholin- Me SO₂CH₂CH₂OMe CF₃ 1-yl 6-1260 morpholin- Me pyrazol-1-yl SO₂Me 1-yl 6-1261 morpholin- Me 4-methoxy- SO₂Me 1-yl pyrazol-1-yl 6-1262 morpholin- Me 1,2,3-triazol-1-yl SO₂Me 1-yl 6-1263 morpholin- Me 1,2,3-triazol-2-yl SO₂Me 1-yl 6-1264 morpholin- Me Cl SO₂Me 1-yl 6-1265 morpholin- Me Me SO₂Me 1-yl 6-1266 morpholin- Me Me SMe 1-yl 6-1267 morpholin- Me SO₂Me Cl 1-yl 6-1268 morpholin- Me NMe₂ SO₂Me 1-yl 6-1269 morpholin- Me NH(CH₂)₂OMe SO₂Me 1-yl 6-1270 morpholin- CF₃ F SO₂CH₃ 1-yl 6-1271 morpholin- CF₃ SMe SO₂CH₃ 1-yl 6-1272 morpholin- CF₃ SEt SO₂CH₃ 1-yl 6-1273 morpholin- CF₃ S(O)Et SO₂CH₃ 1-yl 6-1274 morpholin- CF₃ SO₂CH₃ SO₂CH₃ 1-yl 6-1275 morpholin- CF₃ OCH₂CH₂OMe SO₂CH₃ 1-yl 6-1276 morpholin- CF₃ OCH₂(CO)NMe₂ SO2Me 1-yl 6-1277 morpholin- CF₃ CH₂O- SO₂Et 1-yl tetrahydrofuran-2-yl 6-1278 morpholin- SMe SMe F 1-yl 6-1279 morpholin- SMe SEt F 1-yl 6-1280 morpholin- SO₂CH₃ F Cl 1-yl 6-1281 morpholin- F S(O)Me CF₃ 1-yl 6-1282 morpholin- F SMe CF₃ 1-yl 6-1283 sec-Bu NO₂ H SO₂Me 6-1284 sec-Bu Cl H SO₂Me 6-1285 sec-Bu SO₂Me H CF₃ 6-1286 sec-Bu NO₂ H OMe 6-1287 sec-Bu NO₂ H Br 6-1288 sec-Bu NO₂ H CF₃ 6-1289 sec-Bu NO₂ H NO₂ 6-1290 sec-Bu NO₂ H Cl 6-1291 sec-Bu NO₂ H Me 6-1292 sec-Bu NO₂ H F 6-1293 sec-Bu OMe H SO₂Me 6-1294 sec-Bu CF₃ H NO₂ 6-1295 sec-Bu CH₂SO₂Me H Br 6-1296 sec-Bu Cl CH₂OCH₂CF₃ SO₂Me 6-1297 sec-Bu Cl CH₂OCH₂CF₃ SMe 6-1298 sec-Bu Cl 5-cyanomethyl- SO₂Et 4,5-dihydro- 1,2-oxazol-3-yl 6-1299 sec-Bu Cl 4,5-dihydro-1,2- SO₂Et oxazol-3-yl 6-1300 sec-Bu Cl CH₂OCH₂- SO₂Me tetrahydrofuran-2-yl 6-1301 sec-Bu Cl SMe Cl 6-1302 sec-Bu Cl SMe SO₂Me 6-1303 sec-Bu Cl Me SO₂Et 6-1304 sec-Bu Cl O(CH₂)₂OMe Cl 6-1305 sec-Bu Cl OCH₂-cyclopropyl Cl 6-1306 sec-Bu Cl OMe Cl 6-1307 sec-Bu Cl NHAc Cl 6-1308 sec-Bu Cl OCH₂C(O)NMe₂ Cl 6-1309 sec-Bu Cl Cl SO₂Me 6-1310 sec-Bu Cl pyrazol-1-yl SO₂Me 6-1311 sec-Bu Cl 4-methoxy- SO₂Me pyrazol-1-yl 6-1312 sec-Bu Cl 1,2,3-triazol-1-yl SO₂Me 6-1313 sec-Bu Cl 1,2,3-triazol-2-yl SO₂Me 6-1314 sec-Bu Cl F SO₂Me 6-1315 sec-Bu Me SO₂Me SO₂Me 6-1316 sec-Bu Me SO₂Me CF₃ 6-1317 sec-Bu Me NMe₂ SO₂Me 6-1318 sec-Bu Me S(O)Me CF₃ 6-1319 sec-Bu Me SMe CF₃ 6-1320 sec-Bu Me SO₂CH₂CH₂OMe CF₃ 6-1321 sec-Bu Me pyrazol-1-yl SO₂Me 6-1322 sec-Bu Me 4-methoxy- SO₂Me pyrazol-1-yl 6-1323 sec-Bu Me 1,2,3-triazol-1-yl SO₂Me 6-1324 sec-Bu Me 1,2,3-triazol-2-yl SO₂Me 6-1325 sec-Bu Me Cl SO₂Me 6-1326 sec-Bu Me Me SO₂Me 6-1327 sec-Bu Me Me SMe 6-1328 sec-Bu Me SO₂Me Cl 6-1329 sec-Bu Me NMe₂ SO₂Me 6-1330 sec-Bu Me NH(CH₂)₂OMe SO₂Me 6-1331 sec-Bu CF₃ F SO₂CH₃ 6-1332 sec-Bu CF₃ SMe SO₂CH₃ 6-1333 sec-Bu CF₃ SEt SO₂CH₃ 6-1334 sec-Bu CF₃ S(O)Et SO₂CH₃ 6-1335 sec-Bu CF₃ SO₂CH₃ SO₂CH₃ 6-1336 sec-Bu CF₃ OCH₂CH₂OMe SO₂CH₃ 6-1337 sec-Bu CF₃ OCH₂(CO)NMe₂ SO2Me 6-1338 sec-Bu CF₃ CH₂O- SO₂Et tetrahydrofuran-2-yl 6-1339 sec-Bu SMe SMe F 6-1340 sec-Bu SMe SEt F 6-1341 sec-Bu SO₂CH₃ F Cl 6-1342 sec-Bu F S(O)Me CF₃ 6-1343 sec-Bu F SMe CF₃

TABLE 7 Compounds of the general formula (I) in which A is nitrogen, and R, X, and Z are as defined below.

No. R X Z 7-1 H Cl CF₃ 7-2 Me Cl CF₃ 7-3 Et Cl CF₃ 7-4 CF₃ Cl CF₃ 7-5 CH₂OMe Cl CF₃ 7-6 c-Pr Cl CF₃ 7-7 CO₂Et Cl CF₃ 7-8 CO₂Me Cl CF₃ 7-9 benzyl Cl CF₃ 7-10 phenyl Cl CF₃ 7-11 pyrazin-2-yl Cl CF₃ 7-12 4-OMe—Ph Cl CF₃ 7-13 4-Cl—Ph Cl CF₃ 7-14 t-Bu Cl CF₃ 7-15 furan-2-yl Cl CF₃ 7-16 i-Pr Cl CF₃ 7-17 CH₂CH₂OMe Cl CF₃ 7-18 CH₂CF₃ Cl CF₃ 7-19 tetrahydrofuran- Cl CF₃ 2-yl 7-20 n-Pr Cl CF₃ 7-21 CH₂OEt Cl CF₃ 7-22 cyclobutyl Cl CF₃ 7-23 cyclopentyl Cl CF₃ 7-24 Me₂N Cl CF₃ 7-25 Ph—NH Cl CF₃ 7-26 morpholin-1-yl Cl CF₃ 7-27 H Cl Cl 7-28 Me Cl Cl 7-29 Et Cl Cl 7-30 CF₃ Cl Cl 7-31 CH₂OMe Cl Cl 7-32 c-Pr Cl Cl 7-33 CO₂Et Cl Cl 7-34 CO₂Me Cl Cl 7-35 benzyl Cl Cl 7-36 phenyl Cl Cl 7-37 pyrazin-2-yl Cl Cl 7-38 4-OMe—Ph Cl Cl 7-39 4-Cl—Ph Cl Cl 7-40 t-Bu Cl Cl 7-41 furan-2-yl Cl Cl 7-42 i-Pr Cl Cl 7-43 CH₂CH₂OMe Cl Cl 7-44 CH₂CF₃ Cl Cl 7-45 tetrahydrofuran- Cl Cl 2-yl 7-46 n-Pr Cl Cl 7-47 CH₂OEt Cl Cl 7-48 cyclobutyl Cl Cl 7-49 cyclopentyl Cl Cl 7-50 Me₂N Cl Cl 7-51 Ph—NH Cl Cl 7-52 morpholin-1-yl Cl Cl 7-53 H Me Cl 7-54 Me Me Cl 7-55 Et Me Cl 7-56 CF₃ Me Cl 7-57 CH₂OMe Me Cl 7-58 c-Pr Me Cl 7-59 CO₂Et Me Cl 7-60 CO₂Me Me Cl 7-61 benzyl Me Cl 7-62 phenyl Me Cl 7-63 pyrazin-2-yl Me Cl 7-64 4-OMe—Ph Me Cl 7-65 4-Cl—Ph Me Cl 7-66 t-Bu Me Cl 7-67 furan-2-yl Me Cl 7-68 i-Pr Me Cl 7-69 CH₂CH₂OMe Me Cl 7-70 CH₂CF₃ Me Cl 7-71 tetrahydrofuran- Me Cl 2-yl 7-72 n-Pr Me Cl 7-73 CH₂OEt Me Cl 7-74 cyclobutyl Me Cl 7-75 cyclopentyl Me Cl 7-76 Me₂N Me Cl 7-77 Ph—NH Me Cl 7-78 morpholin-1-yl Me Cl 7-79 H Cl SMe 7-80 Me Cl SMe 7-81 Et Cl SMe 7-82 CF₃ Cl SMe 7-83 CH₂OMe Cl SMe 7-84 c-Pr Cl SMe 7-85 CO₂Et Cl SMe 7-86 CO₂Me Cl SMe 7-87 benzyl Cl SMe 7-88 phenyl Cl SMe 7-89 pyrazin-2-yl Cl SMe 7-90 4-OMe—Ph Cl SMe 7-91 4-Cl—Ph Cl SMe 7-92 t-Bu Cl SMe 7-93 furan-2-yl Cl SMe 7-94 i-Pr Cl SMe 7-95 CH₂CH₂OMe Cl SMe 7-96 CH₂CF₃ Cl SMe 7-97 tetrahydrofuran- Cl SMe 2-yl 7-98 n-Pr Cl SMe 7-99 CH₂OEt Cl SMe 7-100 cyclobutyl Cl SMe 7-101 cyclopentyl Cl SMe 7-102 Me₂N Cl SMe 7-103 Ph—NH Cl SMe 7-104 morpholin-1-yl Cl SMe 7-105 H Cl SO₂Me 7-106 Me Cl SO₂Me 7-107 Et Cl SO₂Me 7-108 CF₃ Cl SO₂Me 7-109 CH₂OMe Cl SO₂Me 7-110 c-Pr Cl SO₂Me 7-111 CO₂Et Cl SO₂Me 7-112 CO₂Me Cl SO₂Me 7-113 benzyl Cl SO₂Me 7-114 phenyl Cl SO₂Me 7-115 pyrazin-2-yl Cl SO₂Me 7-116 4-OMe—Ph Cl SO₂Me 7-117 4-Cl—Ph Cl SO₂Me 7-118 t-Bu Cl SO₂Me 7-119 furan-2-yl Cl SO₂Me 7-120 i-Pr Cl SO₂Me 7-121 CH₂CH₂OMe Cl SO₂Me 7-122 CH₂CF₃ Cl SO₂Me 7-123 tetrahydrofuran- Cl SO₂Me 2-yl 7-124 n-Pr Cl SO₂Me 7-125 CH₂OEt Cl SO₂Me 7-126 cyclobutyl Cl SO₂Me 7-127 cyclopentyl Cl SO₂Me 7-128 Me₂N Cl SO₂Me 7-129 Ph—NH Cl SO₂Me 7-130 morpholin-1-yl Cl SO₂Me 7-131 H Me CF₃ 7-132 Me Me CF₃ 7-133 Et Me CF₃ 7-134 CF₃ Me CF₃ 7-135 CH₂OMe Me CF₃ 7-136 c-Pr Me CF₃ 7-137 CO₂Et Me CF₃ 7-138 CO₂Me Me CF₃ 7-139 benzyl Me CF₃ 7-140 phenyl Me CF₃ 7-141 pyrazin-2-yl Me CF₃ 7-142 4-OMe—Ph Me CF₃ 7-143 4-Cl—Ph Me CF₃ 7-144 t-Bu Me CF₃ 7-145 furan-2-yl Me CF₃ 7-146 i-Pr Me CF₃ 7-147 CH₂CH₂OMe Me CF₃ 7-148 CH₂CF₃ Me CF₃ 7-149 tetrahydrofuran- Me CF₃ 2-yl 7-150 n-Pr Me CF₃ 7-151 CH₂OEt Me CF₃ 7-152 cyclobutyl Me CF₃ 7-153 cyclopentyl Me CF₃ 7-154 Me₂N Me CF₃ 7-155 Ph—NH Me CF₃ 7-156 morpholin-1-yl Me CF₃ 7-157 H CH₂OMe CF₃ 7-158 Me CH₂OMe CF₃ 7-159 Et CH₂OMe CF₃ 7-160 CF₃ CH₂OMe CF₃ 7-161 CH₂OMe CH₂OMe CF₃ 7-162 c-Pr CH₂OMe CF₃ 7-163 CO₂Et CH₂OMe CF₃ 7-164 CO₂Me CH₂OMe CF₃ 7-165 benzyl CH₂OMe CF₃ 7-166 phenyl CH₂OMe CF₃ 7-167 pyrazin-2-yl CH₂OMe CF₃ 7-168 4-OMe—Ph CH₂OMe CF₃ 7-169 4-Cl—Ph CH₂OMe CF₃ 7-170 t-Bu CH₂OMe CF₃ 7-171 furan-2-yl CH₂OMe CF₃ 7-172 i-Pr CH₂OMe CF₃ 7-173 CH₂CH₂OMe CH₂OMe CF₃ 7-174 CH₂CF₃ CH₂OMe CF₃ 7-175 tetrahydrofuran- CH₂OMe CF₃ 2-yl 7-176 n-Pr CH₂OMe CF₃ 7-177 CH₂OEt CH₂OMe CF₃ 7-178 cyclobutyl CH₂OMe CF₃ 7-179 cyclopentyl CH₂OMe CF₃ 7-180 Me₂N CH₂OMe CF₃ 7-181 Ph—NH CH₂OMe CF₃ 7-182 morpholin-1-yl CH₂OMe CF₃ 7-183 H CH₂SMe CF₃ 7-184 Me CH₂SMe CF₃ 7-185 Et CH₂SMe CF₃ 7-186 CF₃ CH₂SMe CF₃ 7-187 CH₂OMe CH₂SMe CF₃ 7-188 c-Pr CH₂SMe CF₃ 7-189 CO₂Et CH₂SMe CF₃ 7-190 CO₂Me CH₂SMe CF₃ 7-191 benzyl CH₂SMe CF₃ 7-192 phenyl CH₂SMe CF₃ 7-193 pyrazin-2-yl CH₂SMe CF₃ 7-194 4-OMe—Ph CH₂SMe CF₃ 7-195 4-Cl—Ph CH₂SMe CF₃ 7-196 t-Bu CH₂SMe CF₃ 7-197 furan-2-yl CH₂SMe CF₃ 7-198 i-Pr CH₂SMe CF₃ 7-199 CH₂CH₂OMe CH₂SMe CF₃ 7-200 CH₂CF₃ CH₂SMe CF₃ 7-201 tetrahydrofuran- CH₂SMe CF₃ 2-yl 7-202 n-Pr CH₂SMe CF₃ 7-203 CH₂OEt CH₂SMe CF₃ 7-204 cyclobutyl CH₂SMe CF₃ 7-205 cyclopentyl CH₂SMe CF₃ 7-206 Me₂N CH₂SMe CF₃ 7-207 Ph—NH CH₂SMe CF₃ 7-208 morpholin-1-yl CH₂SMe CF₃ 7-209 H CH₂SO₂Me CF₃ 7-210 Me CH₂SO₂Me CF₃ 7-211 Et CH₂SO₂Me CF₃ 7-212 CF₃ CH₂SO₂Me CF₃ 7-213 CH₂OMe CH₂SO₂Me CF₃ 7-214 c-Pr CH₂SO₂Me CF₃ 7-215 CO₂Et CH₂SO₂Me CF₃ 7-216 CO₂Me CH₂SO₂Me CF₃ 7-217 benzyl CH₂SO₂Me CF₃ 7-218 phenyl CH₂SO₂Me CF₃ 7-219 pyrazin-2-yl CH₂SO₂Me CF₃ 7-220 4-OMe—Ph CH₂SO₂Me CF₃ 7-221 4-Cl—Ph CH₂SO₂Me CF₃ 7-222 t-Bu CH₂SO₂Me CF₃ 7-223 furan-2-yl CH₂SO₂Me CF₃ 7-224 i-Pr CH₂SO₂Me CF₃ 7-225 CH₂CH₂OMe CH₂SO₂Me CF₃ 7-226 CH₂CF₃ CH₂SO₂Me CF₃ 7-227 tetrahydrofuran- CH₂SO₂Me CF₃ 2-yl 7-228 n-Pr CH₂SO₂Me CF₃ 7-229 CH₂OEt CH₂SO₂Me CF₃ 7-230 cyclobutyl CH₂SO₂Me CF₃ 7-231 cyclopentyl CH₂SO₂Me CF₃ 7-232 Me₂N CH₂SO₂Me CF₃ 7-233 Ph—NH CH₂SO₂Me CF₃ 7-234 morpholin-1-yl CH₂SO₂Me CF₃ 7-235 H CH₂OC₂H₄OMe CF₃ 7-236 Me CH₂OC₂H₄OMe CF₃ 7-237 Et CH₂OC₂H₄OMe CF₃ 7-238 CF₃ CH₂OC₂H₄OMe CF₃ 7-239 CH₂OMe CH₂OC₂H₄OMe CF₃ 7-240 c-Pr CH₂OC₂H₄OMe CF₃ 7-241 CO₂Et CH₂OC₂H₄OMe CF₃ 7-242 CO₂Me CH₂OC₂H₄OMe CF₃ 7-243 benzyl CH₂OC₂H₄OMe CF₃ 7-244 phenyl CH₂OC₂H₄OMe CF₃ 7-245 pyrazin-2-yl CH₂OC₂H₄OMe CF₃ 7-246 4-OMe—Ph CH₂OC₂H₄OMe CF₃ 7-247 4-Cl—Ph CH₂OC₂H₄OMe CF₃ 7-248 t-Bu CH₂OC₂H₄OMe CF₃ 7-249 furan-2-yl CH₂OC₂H₄OMe CF₃ 7-250 i-Pr CH₂OC₂H₄OMe CF₃ 7-251 CH₂CH₂OMe CH₂OC₂H₄OMe CF₃ 7-252 CH₂CF₃ CH₂OC₂H₄OMe CF₃ 7-253 tetrahydrofuran- CH₂OC₂H₄OMe CF₃ 2-yl 7-254 n-Pr CH₂OC₂H₄OMe CF₃ 7-255 CH₂OEt CH₂OC₂H₄OMe CF₃ 7-256 cyclobutyl CH₂OC₂H₄OMe CF₃ 7-257 cyclopentyl CH₂OC₂H₄OMe CF₃ 7-258 Me₂N CH₂OC₂H₄OMe CF₃ 7-259 Ph—NH CH₂OC₂H₄OMe CF₃ 7-260 morpholin-1-yl CH₂OC₂H₄OMe CF₃ 7-261 H OCH₂- CF₃ tetrahydro- furan-2-yl 7-262 Me OCH₂- CF₃ tetrahydro- furan-2-yl 7-263 Et OCH₂- CF₃ tetrahydro- furan-2-yl 7-264 CF₃ OCH₂- CF₃ tetrahydro- furan-2-yl 7-265 CH₂OMe OCH₂- CF₃ tetrahydro- furan-2-yl 7-266 c-Pr OCH₂- CF₃ tetrahydro- furan-2-yl 7-267 CO₂Et OCH₂- CF₃ tetrahydro- furan-2-yl 7-268 CO₂Me OCH₂- CF₃ tetrahydro- furan-2-yl 7-269 benzyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-270 phenyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-271 pyrazin-2-yl OCH₂- CF₃ tetrahydro- furan-2-yl 7-272 4-OMe—Ph OCH₂- CF₃ tetrahydro- furan-2-yl 7-273 4-Cl—Ph OCH₂- CF₃ tetrahydro- furan-2-yl 7-274 t-Bu OCH₂- CF₃ tetrahydro- furan-2-yl 7-275 furan-2-yl OCH₂- CF₃ tetrahydro- furan-2-yl 7-276 i-Pr OCH₂- CF₃ tetrahydro- furan-2-yl 7-277 CH₂CH₂OMe OCH₂- CF₃ tetrahydro- furan-2-yl 7-278 CH₂CF₃ OCH₂- CF₃ tetrahydro- furan-2-yl 7-279 tetrahydro- OCH₂- CF₃ furan-2-yl tetrahydro- furan-2-yl 7-280 n-Pr OCH₂- CF₃ tetrahydro- furan-2-yl 7-281 CH₂OEt OCH₂- CF₃ tetrahydro- furan-2-yl 7-282 cyclobutyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-283 cyclopentyl OCH₂- CF₃ tetrahydro- furan-2-yl 7-284 Me₂N OCH₂- CF₃ tetrahydro- furan-2-yl 7-285 Ph—NH OCH₂- CF₃ tetrahydro- furan-2-yl 7-286 morpholin-1-yl OCH₂- CF₃ tetrahydro- furan-2-yl 7-287 H (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-288 Me (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-289 Et (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-290 CF₃ (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-291 CH₂OMe (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-292 c-Pr (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-293 CO₂Et (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-294 CO₂Me (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-295 benzyl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-296 phenyl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-297 pyrazin-2-yl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-298 4-OMe—Ph (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-299 4-Cl—Ph (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-300 t-Bu (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-301 furan-2-yl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-302 i-Pr (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-303 CH₂CH₂OMe (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-304 CH₂CF₃ (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-305 tetrahydro- (1,1-dioxido-1,2- CF₃ furan-2-yl thiadiazolidin-1- yl)methyl 7-306 n-Pr (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-307 CH₂OEt (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-308 cyclobutyl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-309 cyclopentyl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-310 Me₂N (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-311 Ph—NH (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-312 morpholin-1-yl (1,1-dioxido-1,2- CF₃ thiadiazolidin-1- yl)methyl 7-313 H (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-314 Me (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-315 Et (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-316 CF₃ (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-317 CH₂OMe (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-318 c-Pr (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-319 CO₂Et (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-320 CO₂Me (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-321 benzyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-322 phenyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-323 pyrazin-2-yl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-324 4-OMe—Ph (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-325 4-Cl—Ph (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-326 t-Bu (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-327 furan-2-yl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-328 i-Pr (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-329 CH₂CH₂OMe (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-330 CH₂CF₃ (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-331 tetrahydro- (3-methyl-2- CF₃ furan-2-yl oxoimidazolidin- 1-yl)methyl 7-332 n-Pr (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-333 CH₂OEt (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-334 cyclobutyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-335 cyclopentyl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-336 Me₂N (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-337 Ph—NH (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-338 morpholin-1-yl (3-methyl-2- CF₃ oxoimidazolidin- 1-yl)methyl 7-339 H (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-340 Me (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-341 Et (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-342 CF₃ (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-343 CH₂OMe (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-344 c-Pr (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-345 CO₂Et (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-346 CO₂Me (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-347 benzyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-348 phenyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-349 pyrazin-2-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-350 4-OMe—Ph (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-351 4-Cl—Ph (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-352 t-Bu (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-353 furan-2-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-354 i-Pr (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-355 CH₂CH₂OMe (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-356 CH₂CF₃ (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-357 tetrahydro- (3-methoxy-4- CF₃ furan-2-yl methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-358 n-Pr (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-359 CH₂OEt (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-360 cyclobutyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-361 cyclopentyl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-362 Me₂N (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-363 Ph—NH (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-364 morpholin-1-yl (3-methoxy-4- CF₃ methyl-5-oxo- 4,5-dihydro-1H- 1,2,4-triazol-1- yl)methyl 7-365 i-Pr Cl Me

As already disclosed in WO2012/126932, the compounds of the formula (I) and/or their salts to be used according to the invention, herein below also referred to together as “compounds according to the invention”, have excellent herbicidal efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active compounds act efficiently even on perennial weeds which produce shoots from rhizomes, rootstocks and other perennial organs and which are difficult to control.

The present invention therefore relates to a method for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor herbicides by containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), comprising the application of one or more N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). Specific examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without the enumeration being restricted to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Transgenic crop plants of economically important crops to which the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above might be applied are, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum.

This is why the present invention preferably relates to the method for controlling unwanted plants in areas of transgenic crop plants being tolerant to HPPD inhibitor herbicides by containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gin) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), comprising the application of one or more N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation) in dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum.

It is preferred to use the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum/millet, rice, cassava and maize or else crops of sugar beet, sugar cane, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables, which crops contain one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

The invention also relates to the use, in a method for transforming plants, of a nucleic acid which encodes an HPPD as a marker gene or as a coding sequence which makes it possible to confer to the plant tolerance to herbicides which are HPPD inhibitors, and the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts on plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

In the commercial production of crops, it is desirable to eliminate under reliable pesticidial management unwanted plants (i.e., “weeds”) from a field of crop plants. An ideal treatment would be one which could be applied to an entire field but which would eliminate only the unwanted plants while leaving the crop plants unaffected. One such treatment system would involve the use of crop plants which are tolerant to an herbicide so that when the herbicide is sprayed on a field of herbicide-tolerant crop plants, the crop plants would continue to thrive while non-herbicide-tolerant weeds are killed or severely damaged. Ideally, such treatment systems would take advantage of varying herbicide properties so that weed control could provide the best possible combination of flexibility and economy. For example, individual herbicides have different longevities in the field, and some herbicides persist and are effective for a relatively long time after they are applied to a field while other herbicides are quickly broken down into other and/or non-active compounds. An ideal treatment system would allow the use of different herbicides so that growers could tailor the choice of herbicides for a particular situation.

While a number of herbicide-tolerant crop plants are presently commercially available, one issue that has arisen for many commercial herbicides and herbicide/crop combinations is that individual herbicides typically have incomplete spectrum of activity against common weed species. For most individual herbicides which have been in use for some time, populations of herbicide resistant weed species and biotypes have become more prevalent (see, e.g., Tranel and Wright (2002) Weed Science 50: 700-712; Owen and Zelaya (2005) Pest Manag. Sci. 61: 301-311). Transgenic plants which are resistant to more than one herbicide have been described (see, e.g., WO2005/012515). However, improvements in every aspect of crop production, weed control options, extension of residual weed control, and improvement in crop yield are continuously in demand.

The above defined chimeric gene(s) encoding one or more HPPD protein(s) or mutants thereof being functional in transgenic plants in order to perform tolerance to HPPD inhibitor herbicides belonging to the class of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts is/are advantageously combined in plants with other genes which encode proteins or RNAs that confer useful agronomic properties to such plants. Among the genes which encode proteins or RNAs that confer useful agronomic properties on the transformed plants, mention can be made of the DNA sequences encoding proteins which confer tolerance to one or more herbicides that, according to their chemical structure, differ from HPPD inhibitor herbicides, and others which confer tolerance to certain insects, those which confer tolerance to certain diseases and or biotic and abiotic stresses, DNAs that encodes RNAs that provide nematode or insect control, etc.

Such genes are in particular described in published PCT Patent Applications WO 91/02071 and WO95/06128.

Among the DNA sequences encoding proteins which confer tolerance to certain herbicides on the transformed plant cells and plants, mention can be made of a bar or PAT gene or the Streptomyces coelicolor gene described in WO2009/152359 which confers tolerance to glufosinate herbicides, a gene encoding a suitable EPSPS which confers tolerance to herbicides having EPSPS as a target, such as glyphosate and its salts (U.S. Pat. Nos. 4,535,060, 4,769,061, 5,094,945, 4,940,835, 5,188,642, 4,971,908, 5,145,783, 5,310,667, 5,312,910, 5,627,061, 5,633,435), or a gene encoding glyphosate oxydoreductase (U.S. Pat. No. 5,463,175).

Among the DNA sequences encoding a suitable EPSPS which confer tolerance to the herbicides which have EPSPS as a target, mention will more particularly be made of the gene which encodes a plant EPSPS, in particular maize EPSPS, particularly a maize EPSPS which comprises two mutations, particularly a mutation at amino acid position 102 and a mutation at amino acid position 106 (WO 2004/074443), and which is described in Patent Application U.S. Pat. No. 6,566,587, hereinafter named double mutant maize EPSPS or 2 mEPSPS, or the gene which encodes an EPSPS isolated from Agrobacterium and which is described by SEQ ID No. 2 and SEQ ID No. 3 of U.S. Pat. No. 5,633,435, also named CP4.

Among the DNA sequences encoding a suitable EPSPS which confer tolerance to the herbicides which have EPSPS as a target, mention will more particularly be made of the gene which encodes an EPSPS GRG23 from Arthrobacter globiformis, but also the mutants GRG23 ACE1, GRG23 ACE2, or GRG23 ACE3, particularly the mutants or variants of GRG23 as described in WO2008/100353, such as GRG23(ace3)R173K of SEQ ID No. 29 in WO2008/100353.

In the case of the DNA sequences encoding EPSPS, and more particularly encoding the above genes, the sequence encoding these enzymes is advantageously preceded by a sequence encoding a transit peptide, in particular the “optimized transit peptide” described in U.S. Pat. No. 5,510,471 or U.S. Pat. No. 5,633,448.

In WO 2007/024782, plants being tolerant to glyphosate and at least one ALS (acetolactate synthase) inhibitor are disclosed. More specifically plants containing genes encoding a GAT (Glyphosate-N-Acetyltransferase) polypeptide and a polypeptide conferring resistance to ALS inhibitors are disclosed.

In U.S. Pat. No. 6,855,533, transgenic tobacco plants containing mutated Arabidopsis ALS/AHAS genes were disclosed.

In U.S. Pat. No. 6,153,401, plants containing genes encoding 2,4-D-monooxygenases conferring tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid) by metabolisation are disclosed.

In US 2008/0119361 and US 2008/0120739, plants containing genes encoding Dicamba monooxygenases conferring tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid) by metabolisation are disclosed.

In WO2011/028833 and WO2011/028832 plants containing genes encoding mutagenized or recombinant Acetyl-coenzyme-A carboxylase (ACCase) conferring tolerance to at least one herbicide is selected from the group consisting of alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, sethoxydim, tepraloxydim, tralkoxydim, chlorazifop, clodinafop, clofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, propaquizafop, quizalofop, quizalofop-P, trifop, and pinoxaden or agronomically acceptable salts or esters of any of these herbicides are disclosed.

All the above mentioned herbicide tolerance traits can be combined with those performing HPPD tolerance in plants concerning N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts by containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

Among the DNA sequences encoding proteins concerning properties of tolerance to insects, mention will more particularly be made of the Bt proteins widely described in the literature and well known to those skilled in the art. Mention will also be made of proteins extracted from bacteria such as Photorhabdus (WO 97/17432 & WO 98/08932). Among such DNA sequences encoding proteins of interest which confer novel properties of tolerance to insects, mention will more particularly be made of the Bt Cry or VIP proteins widely described in the literature and well known to those skilled in the art. These include the Cry1F protein or hybrids derived from a Cry1F protein (e.g., the hybrid Cry1A-Cry1F proteins described in U.S. Pat. Nos. 6,326,169; 6,281,016; 6,218,188, or toxic fragments thereof), the Cry1A-type proteins or toxic fragments thereof, preferably the Cry1Ac protein or hybrids derived from the Cry1Ac protein (e.g., the hybrid Cry1Ab-Cry1Ac protein described in U.S. Pat. No. 5,880,275) or the Cry1Ab or Bt2 protein or insecticidal fragments thereof as described in EP451878, the Cry2Ae, Cry2Af or Cry2Ag proteins as described in WO02/057664 or toxic fragments thereof, the Cry1A. 105 protein described in WO 2007/140256 (SEQ ID No. 7) or a toxic fragment thereof, the VIP3Aa19 protein of NCBI accession ABG20428, the VIP3Aa20 protein of NCBI accession ABG20429 (SEQ ID No. 2 in WO 2007/142840), the VIP3A proteins produced in the COT202 or COT203 cotton events (WO 2005/054479 and WO 2005/054480, respectively), the Cry proteins as described in WO01/47952, the VIP3Aa protein or a toxic fragment thereof as described in Estruch et al. (1996), Proc Natl Acad Sci USA. 28; 93(11):5389-94 and U.S. Pat. No. 6,291,156, the insecticidal proteins from Xenorhabdus (as described in WO98/50427), Serratia (particularly from S. entomophila) or Photorhabdus species strains, such as Tc-proteins from Photorhabdus as described in WO98/08932 (e.g., Waterfield et al., 2001, Appl Environ Microbiol. 67(11):5017-24; Ffrench-Constant and Bowen, 2000, Cell Mol Life Sci.; 57(5):828-33). Also any variants or mutants of any one of these proteins differing in some (1-10, preferably 1-5) amino acids from any of the above sequences, particularly the sequence of their toxic fragment, or which are fused to a transit peptide, such as a plastid transit peptide, or another protein or peptide, is included herein.

The present invention also relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts in transgenic plants comprising a chimeric gene (or expression cassette) which comprises a coding sequence as well as heterologous regulatory elements, at the 5′ and/or 3′ position, at least at the 5′ position, which are able to function in a host organism, in particular plant cells or plants, with the coding sequence containing at least one nucleic acid sequence which encodes an HPPD (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

In another particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts in transgenic plant comprising a chimeric gene as previously described, wherein the chimeric gene contains in the 5′ position of the nucleic acid sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) (I) derived from a member of a group of organisms, consisting of (a) 10 Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), a nucleic acid sequence which encodes a plant transit peptide, with this sequence being arranged between the promoter region and the nucleic acid sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (11) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (III) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), so as to permit expression of a transit peptide/HPPD fusion protein.

In a further particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxam ides as defined above or their salts on plants, plant parts, or plant seeds containing one or more chimeric gene(s) (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), or to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts on soil where such plants, plant parts or seeds are to be grown or sown, either alone or in combination with one or more other known herbicides acting in a different matter to HPPD inhibitors.

In a further particular embodiment, the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts herbicide can applied in combination either in mixture, simultaneously or successively with HPPD inhibitor herbicides selected from the group consisting of triketones (named triketone HPPD inhibitor), such as tembotrione, sulcotrione mesotrione, bicyclopyrone, tefuryltrione, particularly tembotrione, of the class diketone such as diketonitrile of the class of isoxazoles such as isoxaflutole or of the class of pyrazolinates (named pyrazolinate HPPD inhibitor), such as pyrasulfotole, pyrazolate, topramezone, benzofenap, even more specifically present invention relates to the application of tembotrione, mesotrione, diketonitrile, bicyclopyrone, tefuryltrione, benzofenap, pyrasulfotole, pyrazolate and sulcotrione to such HPPD inhibitor tolerant plants, plant parts or plant seeds containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

As a regulatory sequence which functions as a promoter in plant cells and plants, use may be made of any promoter sequence of a gene which is naturally expressed in plants, in particular a promoter which is expressed especially in the leaves of plants, such as for example “constitutive” promoters of bacterial, viral or plant origin, or “light-dependent” promoters, such as that of a plant ribulose-biscarboxylase/oxygenase (RuBisCO) small subunit gene, or any suitable known promoter-expressible which may be used. Among the promoters of plant origin, mention will be made of the histone promoters as described in EP 0 507 698 A1, the rice actin promoter (U.S. Pat. No. 5,641,876), or a plant ubiquitin promoter (U.S. Pat. No. 5,510,474). Among the promoters of a plant virus gene, mention will be made of that of the cauliflower mosaic virus (CaMV 19S or 35S, Sanders et al. (1987), Nucleic Acids Res. 15(4):1543-58), the circovirus (AU 689 311) or the Cassava vein mosaic virus (CsVMV, U.S. Pat. No. 7,053,205).

In a further particular embodiment, present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxam ides as defined above or their salts on plants, plant parts, or plant seeds comprising a promoter sequence specific for particular regions or tissues of plants can be used to express one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (11) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), such as promoters specific for seeds (Datla, R. et al., 1997, Biotechnology Ann. Rev. 3, 269-296), especially the napin promoter (EP 255 378 A1), the phaseolin promoter, the glutenin promoter, the helianthinin promoter (WO 92/17580), the albumin promoter (WO 98/45460), the oleosin promoter (WO 98/45461), the SAT1 promoter or the SAT3 promoter (PCT/US98/06978).

Use may also be made of an inducible promoter advantageously chosen from the phenylalanine ammonia lyase (PAL), HMG-CoA reductase (HMG), chitinase, glucanase, proteinase inhibitor (PI), PR1 family gene, nopaline synthase (nos) and vspB promoters (U.S. Pat. No. 5,670,349, Table 3), the HMG2 promoter (U.S. Pat. No. 5,670,349), the apple beta-galactosidase (ABG1) promoter and the apple aminocyclopropane carboxylate synthase (ACC synthase) promoter (WO 98/45445).

The genes encoding hydroxyphenylpyruvate dioxygenase (HPPD) (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) may also be used in combination with the promoter, of other regulatory sequences, which are located between the promoter and the coding sequence, such as transcription activators (“enhancers”), for instance the translation activator of the tobacco mosaic virus (TMV) described in Application WO 87/07644, or of the tobacco etch virus (TEV) described by Carrington & Freed 1990, J. Virol. 64: 1590-1597, for example, or introns such as the adh1 intron of maize or intron 1 of rice actin in order to perform a sufficient tolerance to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts.

In a further particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts on plants, plant parts, or plant seeds containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (11) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (111) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) and also containing a CYP450 Maize monooxygenase (nsf1 gene) gene being under the control of an identical or different plant expressible promoter in order to confer tolerance to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts.

As a regulatory terminator or polyadenylation sequence, use may be made of any corresponding sequence of bacterial origin, such as for example the nos terminator of Agrobacterium tumefaciens, of viral origin, such as for example the CaMV 35S terminator, or of plant origin, such as for example a histone terminator as described in published Patent Application EP 0 633 317 A1.

It is to be understood that in order to obtain an optimized expression by a host adapted codon usage of the respective chimeric gene(s), one could adopt non-planta genes to the codon usage of the respective plant organism in which such chimeric genes will be inserted. Accordingly, in all of the described chimeric genes expressing HPPD of non-planta origin, the respective HPPD encoding DNA sequence can be replaced by an amended DNA sequence encoding the identical amino acid sequence, i.e. SEQ ID No. 3 can be replaced by SEQ ID No. 5, SEQ ID No. 6 can be replaced by SEQ ID No. 18, SEQ ID No. 8 can be replaced by SEQ ID No. 19, SEQ ID No. 10 can be replaced by SEQ ID No. 20, SEQ ID No. 12 can be replaced by SEQ ID No. 21, SEQ ID No. 14 can be replaced by SEQ ID No. 22, SEQ ID No, 16 can be replace by SEQ ID No. 23.

The term “gene”, as used herein refers to a DNA coding region flanked by 5′ and/or 3′ regulatory sequences allowing RNA to be transcribed which can be translated to a protein, typically comprising at least a promoter region. A “chimeric gene”, when referring to an HPPD encoding DNA, refers to an HPPD encoding DNA sequence having 5′ and/or 3′ regulatory sequences different from the naturally occurring bacterial 5′ and/or 3′ regulatory sequences which drive the expression of the HPPD protein in its native host cell (also referred to as “heterologous promoter” or “heterologous regulatory sequences”).

The terms “DNA/protein comprising the sequence X” and “DNA/protein with the sequence comprising sequence X”, as used herein, refer to a DNA or protein including or containing at least the sequence X in their nucleotide or amino acid sequence, so that other nucleotide or amino acid sequences can be included at the 5′ (or N-terminal) and/or 3′ (or C-terminal) end, e.g., a N-terminal transit or signal peptide. The term “comprising”, as used herein, is open-ended language in the meaning of “including”, meaning that other elements then those specifically recited can also be present. The term “consisting of”, as used herein, is closed-ended language, i.e., only those elements specifically recited are present. The term “DNA encoding a protein comprising sequence X”, as used herein, refers to a DNA comprising a coding sequence which after transcription and translation results in a protein containing at least amino acid sequence X. A DNA encoding a protein need not be a naturally occurring DNA, and can be a semi-synthetic, fully synthetic or artificial DNA and can include introns and 5′ and/or 3′ flanking regions. The term “nucleotide sequence”, as used herein, refers to the sequence of a DNA or RNA molecule, which can be in single- or double-stranded form.

HPPD proteins according to the invention may be equipped with a signal peptide according to procedures known in the art, see, e.g., published PCT patent application WO 96/10083, or they can be replaced by another peptide such as a chloroplast transit peptide (e.g., Van Den Broeck et al., 1985, Nature 313, 358, or a modified chloroplast transit peptide of U.S. Pat. No. 5,510,471) causing transport of the protein to the chloroplasts, by a secretory signal peptide or a peptide targeting the protein to other plastids, mitochondria, the ER, or another organelle, or it can be replaced by a methionine amino acid or by a methionine-alanine dipeptide. Signal sequences for targeting to intracellular organelles or for secretion outside the plant cell or to the cell wall are found in naturally targeted or secreted proteins, preferably those described by Klsgen et al. (1989, Mol. Gen. Genet. 217, 155-161), Klsgen and Weil (1991, Mol. Gen. Genet. 225, 297-304), Neuhaus & Rogers (1998, Plant Mol. Biol. 38, 127-144), Bih et al. (1999, J. Biol. Chem. 274, 22884-22894), Morris et al. (1999, Biochem. Biophys. Res. Commun. 255, 328-333), Hesse et al. (1989, EMBO J. 8 2453-2461), Tavladoraki et al. (1998, FEBS Lett. 426, 62-66), Terashima et al. (1999, Appl. Microbiol. Biotechnol. 52, 516-523), Park et al. (1997, J. Biol. Chem. 272, 6876-6881), Shcherban et al. (1995, Proc. Natl. Acad. Sci USA 92, 9245-9249), all of which are incorporated herein by reference, particularly the signal peptide sequences from targeted or secreted proteins of corn, cotton, soybean, or rice. A DNA sequence encoding such a plant signal peptide can be inserted in the chimeric gene encoding the HPPD protein for expression in plants.

The invention also encompasses variant HPPD enzymes which are amino acid sequences similar to the HPPD amino acid sequence of SEQ ID No. 2, SEQ ID No. ID No. 4, SEQ ID No. 7, SEQ ID No. 9, SEQ ID No. 11, SEQ ID No. 13, SEQ ID No. 15, and SEQ ID No. 17 wherein in each of the before one or more amino acids have been inserted, deleted or substituted. In the present context, variants of an amino acid sequence refer to those polypeptides, enzymes or proteins which have a similar catalytic activity as the amino acid sequences described herein, notwithstanding any amino acid substitutions, additions or deletions thereto. Preferably the variant amino acid sequence has a sequence identity of at least about 80%, or 85 or 90%, 95%, 97%, 98% or 99% with the amino acid sequence of SEQ ID No. 2, SEQ ID No. 4, SEQ ID No. 7, SEQ ID No. 9, SEQ ID No. 11, SEQ ID No. 13, SEQ ID No. 15, and SEQ ID No. 17, respectively. Also preferably, a polypeptide comprising the variant amino acid sequence has HPPD enzymatic activity. Methods to determine HPPD enzymatic activity are well known in the art and include assays as extensively described in WO 2009/144079 or in WO 2002/046387, or in PCT/EP2010/070561.

Substitutions encompass amino acid alterations in which an amino acid is replaced with a different naturally-occurring or a non-conventional amino acid residue. Such substitutions may be classified as “conservative”, in which an amino acid residue contained in an HPPD protein of this invention is replaced with another naturally-occurring amino acid of similar character, for example Gly↔Ala, Val↔Ile↔Leu, Asp↔Glu, Lys↔Arg, Asn↔Gln or Phe↔Trp↔Tyr. Substitutions encompassed by the present invention may also be “non-conservative”, in which an amino acid residue which is present in an HPPD protein of the invention is substituted with an amino acid with different properties, such as a naturally-occurring amino acid from a different group (e.g. substituting a charged or hydrophobic amino acid with alanine. Amino acid substitutions are typically of single residues, but may be of multiple residues, either clustered or dispersed. Amino acid deletions will usually be of the order of about 1-10 amino acid residues, while insertions may be of any length. Deletions and insertions may be made to the N-terminus, the C-terminus or be internal deletions or insertions. Generally, insertions within the amino acid sequence will be smaller than amino- or carboxy-terminal fusions and of the order of 1 to 4 amino acid residues. “Similar amino acids”, as used herein, refers to amino acids that have similar amino acid side chains, i.e. amino acids that have polar, non-polar or practically neutral side chains. “Non-similar amino acids”, as used herein, refers to amino acids that have different amino acid side chains, for example an amino acid with a polar side chain is non-similar to an amino acid with a non-polar side chain. Polar side chains usually tend to be present on the surface of a protein where they can interact with the aqueous environment found in cells (“hydrophilic” amino acids). On the other hand, “non-polar” amino acids tend to reside within the center of the protein where they can interact with similar non-polar neighbors (“hydrophobic” amino acids”). Examples of amino acids that have polar side chains are arginine, asparagine, aspartate, cysteine, glutamine, glutamate, histidine, lysine, serine, and threonine (all hydrophilic, except for cysteine which is hydrophobic). Examples of amino acids that have non-polar side chains are alanine, glycine, isoleucine, leucine, methionine, phenylalanine, proline, and tryptophan (all hydrophobic, except for glycine which is neutral).

Unless otherwise stated in the examples, all procedures for making and manipulating recombinant DNA are carried out by the standard procedures described in Sambrook et al., Molecular Cloning—A Laboratory Manual, Second Ed., Cold Spring Harbor Laboratory Press, NY (1989), and in Volumes 1 and 2 of Ausubel et al. (1994) Current Protocols in Molecular Biology, Current Protocols, USA. Standard materials and methods for plant molecular biology work are described in Plant Molecular Biology Labfax (1993) by R. R. D. Croy, jointly published by BIOS Scientific Publications Ltd (UK) and Blackwell Scientific Publications (UK). Procedures for PCR technology can be found in “PCR protocols: a guide to methods and applications”, Edited by M. A. Innis, D. H. Gelfand, J. J. Sninsky and T. J. White (Academic Press, Inc., 1990).

The terms “tolerance”, “tolerant” or “less sensitive” are interchangeable used and mean the relative levels of inherent tolerance of the HPPD screened according to a visible indicator phenotype of the strain or plant transformed with a nucleic acid comprising the gene coding for the respective HPPD protein in the presence of different concentrations of the various HPPD inhibitor herbicides. Dose responses and relative shifts in dose responses associated with these indicator phenotypes (formation of brown color, growth inhibition, bleaching, herbicidal effect, etc.) are conveniently expressed in terms, for example, of GR50 (concentration for 50% reduction of growth) or MIC (minimum inhibitory concentration) values where increases in values correspond to increases in inherent tolerance of the expressed HPPD, in the normal manner based upon plant damage, meristematic bleaching symptoms etc. at a range of different concentrations of herbicides. These data can be expressed in terms of, for example, GR50 values derived from dose/response curves having “dose” plotted on the x-axis and “percentage kill”, “herbicidal effect”, “numbers of emerging green plants” etc. plotted on the y-axis where increased GR50 values correspond to increased levels of inherent tolerance of the expressed HPPD. Herbicides can suitably be applied pre-emergence or post emergence.

Likewise, tolerance level is screened via transgenesis, regeneration, breeding and spray testing of a test plant such as tobacco, or a crop plant such as soybean or cotton and according to these results, such plants are at least 2-4× more tolerant to HPPD inhibitor herbicides, like N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts than plants that do not contain any exogenous gene encoding an HPPD protein, “Host organism” or “host” is understood as being any unicellular or multicellular heterologous organism into which the nucleic acid or chimeric gene according to the invention can be introduced for the purpose of producing HPPD. These organisms are, in particular, bacteria, for example E. coli, yeast, in particular of the genera Saccharomyces or Kluyveromyces, Pichia, fungi, in particular Aspergillus, a baculovirus or, preferably, plant cells and plants.

“Plant cell” is understood, according to the invention, as being any cell which is derived from or found in a plant and which is able to form or is part of undifferentiated tissues, such as calli, differentiated tissues such as embryos, parts of plants, plants or seeds. This includes protoplasts and pollen, cultivated plants cells or protoplasts grown in vitro, and plant cells that can regenerate into a complete plant.

“Plant” is understood, according to the invention, as being any differentiated multicellular organism which is capable of photosynthesis, in particular a monocotyledonous or dicotyledonous organism, more especially cultivated plants which are or are not intended for animal or human nutrition, such as maize or corn, wheat, Brassica spp. plants such as Brassica napus or Brassica juncea, soya spp, rice, sugarcane, beetroot, tobacco, cotton, vegetable plants such as cucumber, leek, carrot, tomato, lettuce, peppers, melon, watermelon, etc. Transgenic plants, as used herein, refer to plants comprising one or more foreign or heterologous gene(s) stably inserted in their genome.

In order perform tolerance to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts, any promoter sequence of a gene which is expressed naturally in plants, or any hybrid or combination of promoter elements of genes expressed naturally in plants, including Agrobacterium or plant virus promoters, or any promoter which is suitable for controlling the transcription of a herbicide tolerance gene in plants, can be used as the promoter sequence in the plants of the invention (named “plant-expressible promoter” herein). Examples of such suitable plant-expressible promoters are described above. In one embodiment of this invention, such plant-expressible promoters are operably-linked to a (I) DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) that is derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (11) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

According to the invention, it is also possible to use, in combination with the promoter regulatory sequence, other regulatory sequences which are located between the promoter and the coding sequence, such as intron sequences, or transcription activators (enhancers) in order to perform tolerance to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts. Examples of such suitable regulatory sequences are described above.

Any corresponding sequence of bacterial or viral origin, such as the nos terminator from Agrobacterium tumefaciens, or of plant origin, such as a histone terminator as described in application EP 0 633 317 A1, may be used as transcription termination (and polyadenylation) regulatory sequence.

In a further particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxam ides as defined above or their salts on plants, plant parts, or plant seeds containing a nucleic acid sequence which encodes a transit peptide is employed 5′ (upstream) of the nucleic acid sequence encoding the exogenous chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) and also containing with this transit peptide sequence being arranged between the promoter region and the sequence encoding the exogenous HPPD so as to permit expression of a transit peptide-HPPD fusion protein. The transit peptide makes it possible to direct the HPPD into the plastids, more especially the chloroplasts, with the fusion protein being cleaved between the transit peptide and the HPPD protein when the latter enters the plastid. The transit peptide may be a single peptide, such as an EPSPS transit peptide (described in U.S. Pat. No. 5,188,642) or a transit peptide of the plant ribulose bisphosphate carboxylase/oxygenase small subunit (RuBisCO ssu), where appropriate, including a few amino acids of the N-terminal part of the mature RuBisCO ssu (EP 189 707 A1), or else may be a fusion of several transit peptides such as a transit peptide which comprises a first plant transit peptide which is fused to a part of the N-terminal sequence of a mature protein having a plastid location, with this part in turn being fused to a second plant transit peptide as described in patent EP 508 909 A1, and, more especially, the optimized transit peptide which comprises a transit peptide of the sunflower RuBisCO ssu fused to 22 amino acids of the N-terminal end of the maize RuBisCO ssu, in turn fused to the transit peptide of the maize RuBisCO ssu, as described, with its coding sequence, in patent EP 508 909 A1.

The present invention also relates to the transit peptide HPPD fusion protein and a nucleic acid or plant-expressible chimeric gene encoding such fusion protein, wherein the two elements of this fusion protein are as defined above.

In a further particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts on plants, plant parts, or plant seeds obtained by cloning, transformation with an expression vector, which expression vector contains at least one chimeric gene encoding the hydroxyphenylpyruvate dioxygenase (HPPD) (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37). In addition to the above chimeric gene, this vector can contain an origin of replication. This vector can be a plasmid or plasmid portion, a cosmid, or a bacteriophage or a virus which has been transformed by introducing the chimeric gene according to the invention. Transformation vectors are well known to the skilled person and widely described in the literature. The transformation vector which can be used, in particular, for transforming plant cells or plants may be a virus, which can be employed for transforming plant cells or plants and which additionally contains its own replication and expression elements. The vector for transforming plant cells or plants is preferably a plasmid, such as a disarmed Agrobacterium Ti plasmid.

In a further particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts on plants, plant parts, or plant seeds containing a chimeric gene which comprises a sequence encoding the hydroxyphenylpyruvate dioxygenase (HPPD) (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (11) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (111) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), and the use of the plants or seeds in a field to grow a crop and harvest a plant product, e.g., soya spp, rice, wheat, barley or corn grains or cotton bolls, where in one embodiment said use involves the application of an N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to such plants to control weeds.

In another particular embodiment, the present invention relates to the use of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts on plants, plant parts, or plant seeds characterized in that it contains one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (11) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) and in addition further contains a chimeric gene comprising a plant-expressible promoter as described above, operably-linked to a nucleic acid sequence encoding a PDH (prephenate dehydrogenase) enzyme (US 2005/0257283) in order to confer tolerance to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts. A plant comprising such two transgenes can be obtained by transforming a plant with one transgene, and then re-transforming this transgenic plant with the second transgene, or by transforming a plant with the two transgenes simultaneously (in the same or in 2 different transforming DNAs or vectors), or by crossing a plant comprising the first transgene with a plant comprising the second transgene, as is well known in the art.

One transformation method in order to obtain plants, plant parts or seeds being tolerant to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts by containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) comprises bombarding cells, protoplasts or tissues with solid or liquid particles to which DNA is attached, or containing DNA. Another transformation method comprises using, as mean for transfer into the plant, a chimeric gene which is inserted into an Agrobacterium tumefaciens Ti plasmid or an Agrobacterium rhizogenes Ri plasmid. Other methods may be used, such as microinjection or electroporation or otherwise direct gene transfer using PEG. The skilled person can select any appropriate method for transforming the host organism of choice, in particular the plant cell or the plant. As examples, the technology for soybean transformation has been extensively described in the examples 1 to 3 disclosed in EP 1186666 A1, incorporated herein by reference. For rice, Agrobacterium-mediated transformation (Hiei et al., 1994 Plant J 6:271-282, and Hiei et al., 1997 Plant Mol Biol. 35:205-21, incorporated herein by reference), electroporation (U.S. Pat. No. 5,641,664and U.S. Pat. No. 5,679,558, incorporated herein by reference), or bombardment (Christou et al., 1991, Biotechnology 9:957 incorporated herein by reference) could be performed. A suitable technology for transformation of monocotyledonous plants, and particularly rice, is described in WO 92/09696, incorporated herein by reference. For cotton, Agrobacterium-mediated transformation (Gould J. H. and Magallanes-Cedeno M., 1998 Plant Molecular Biology reporter, 16:1-10 and Zapata C., 1999, Theoretical Applied Genetics, 98(2):1432-2242 incorporated herein by reference), polybrene and/or treatment-mediated transformation (Sawahel W. A., 2001,—Plant Molecular Biology reporter, 19:377a-377f, incorporated herein by reference) have been described.

Alternatively, N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts may be used on plants, plant parts, or plant seeds containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) which HPPD is expressed directly in the plastids, such as the chloroplasts, using transformation of the plastid, such as the chloroplast genome. A suitable method comprises the bombardment of plant cells or tissue by solid particles coated with the DNA or liquid particles comprising the DNA, and integration of the introduced gene by homologous recombination. Suitable vectors and selection systems are known to the person skilled in the art. An example of means and methods which can be used for such integration into the chloroplast genome of tobacco plants is given in WO 06/108830, the content of which is hereby incorporated by reference

The present invention also relates to a method for obtaining a plant tolerant to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts, characterized in that the plant is transformed with one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (h) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

Therefore, the present invention also relates to a method for obtaining a plant tolerant to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts by containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), which comprises a coding sequence as well as a heterologous regulatory element in the 5′ and optionally in the 3′ positions, which are able to function in a host organism, characterized in that the coding sequence comprises at least a nucleic acid sequence defining a gene encoding an HPPD of the invention as previously described in order to perform a sufficiently high level of tolerance to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts.

In one embodiment of this invention, the HPPD inhibitor in the above method is a N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts either alone or in combination with one or more HPPD inhibitor herbicides selected from the group consisting of triketone or pyrazolinate herbicide, preferably tembotrione, mesotrione, bicyclopyrone, tefuryltrione pyrasulfotole, pyrazolate, diketonitrile, benzofenap, or sulcotrione, particularly tembotrione.

The invention also relates to a method for selectively removing weeds or preventing the germination of weeds in a field to be planted with plants or to be sown with seeds, or in a plant crop, by application of a N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to such field or plant crop, which method is characterized in that this N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts is applied to plants which have been transformed in accordance with one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), either before sowing the crop (hereinafter named pre-planting application), before emergence of the crop (hereinafter named pre-emergence application), or after emergence of the crop (hereinafter named post-emergence application).

The invention also relates to a method for controlling in an area or a field which contains transformed seeds as previously described in the present invention, which method comprises applying, to the said area of the field, a dose of an N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts which is toxic for the said weeds, without significantly affecting the seeds or plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).

The present invention also relates to a method for cultivating the plants which have been transformed with one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37). which method comprises planting seeds comprising a chimeric gene of before, in an area of a field which is appropriate for cultivating the said plants, and in applying, if weeds are present, a dose, which is toxic for the weeds, of one or more N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to the said area of the said field, without significantly affecting the said transformed seeds or the said transformed plants, and in then harvesting the cultivated plants or plant parts when they reach the desired stage of maturity and, where appropriate, in separating the seeds from the harvested plants.

In the above methods, the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts can be applied in accordance with the invention, either before sowing the crop, before the crop emerges or after the crop emerges.

Within the meaning of the present invention, “herbicide” is understood as being a herbicidally active substance on its own or such a substance which is combined with an additive which alters its efficacy, such as, for example, an agent which increases its activity (a synergistic agent) or which limits its activity (a safener). It is of course to be understood that, for their application in practice, the above herbicides are combined, in a manner which is known per se, with the formulation adjuvants which are customarily employed in agricultural chemistry.

Thus, transgenic plants can be obtained which—in addition to the one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37).—have modified properties as the result of overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

On the plants, plant cells or seeds containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), it is preferred to employ one or more of the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts in combination with one or more further HPPD inhibitor herbicides belonging to the class of triketones, such as tembotrione, sulcotrione and mesotrione, or of the class of pyrazolinates, such as pyrasulfotole and topramezone, particularly selected from tembotrione, sulcotrione, topramezone, bicyclopyrone, tefuryltrione and mesotrione, more particularly tembotrione in transgenic crops which are also resistant to growth regulators such as, for example, 2,4-D or dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), Acetyl-coenzyme A carboxylase (ACCase), or against herbicides from the group of the sulfonylureas, imidazolinones, glyphosate, glufosinate, ACCase inhibitors and analogous active substances.

The invention therefore also relates to the use of herbicides applied to HPPD tolerant plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) for controlling harmful plants (i.e. weeds) which also extends to transgenic crop plants comprising a second or more herbicide resistance(s) beside the resistance against one or more N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts.

N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts can be formulated in various ways, depending on the prevailing biological and/or physico-chemical parameters. Examples of possible formulations are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing products, granules for application by broadcasting and on the soil, granules (GR) in the form of micro granules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kichler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are also known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kichler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.

Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants (wetters, dispersers), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate, besides a diluent or inert substance. To prepare the wettable powders, the herbicidally active substances are ground finely, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and mixed with the formulation auxiliaries, either simultaneously or subsequently.

Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters such as, for example, sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as, for example, polyoxyethylene sorbitan fatty acid esters. Dusts are obtained by grinding the active substance with finely divided solid materials such as, for example, talcum, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can be prepared for example by wet-grinding by means of commercially available bead mills, if appropriate with addition of surfactants as already listed above for example in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if appropriate, surfactants, as have already been mentioned for example above for the other formulation types.

Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material, or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of stickers, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is customary for the production of fertilizer granules, if desired as a mixture with fertilizers.

Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed stirrers, and extrusion without solid inert material.

To prepare disk granules, fluidized-bed granules, extruder granules and spray granules, see, for example, methods in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 et seq.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.

For further details of the formulation of crop protection products see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical preparations comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration can amount to approximately 1 to 90, preferably 5 to 80% by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active substance, preferably in most cases from 5 to 20% by weight of active substance, and sprayable solutions comprise approximately from 0.05 to 80, preferably from 2 to 50% by weight of active substance. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers and the like which are being used. In the case of the water-dispersible granules, for example, the active substance content is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active substance formulations mentioned comprise, if appropriate, the auxiliaries which are conventional in each case, such as stickers, wetters, dispersants, emulsifiers, penetrations, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors, and pH and viscosity regulators.

Based on these formulations, it is also possible to prepare combinations of an HPPD inhibitor herbicide of the class of triketones, such as tembotrione, sulcotrione and mesotrione, or of the class of pyrazolinates, such as pyrasulfotole and topramezone, particularly selected from tembotrione, sulcotrione, topramezone, bicyclopyrone, tefuryltrione and mesotrione, more particularly tembotrione with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix to be applied to HPPD tolerant plants according to the invention.

FORMULATION EXAMPLES

-   -   a) A dust is obtained by mixing 10 parts by weight of a compound         of the formula (I) and/or a salt thereof and 90 parts by weight         of talc as inert substance and comminuting the mixture in a         hammer mill.     -   b) A wettable powder which is readily dispersible in water is         obtained by mixing 25 parts by weight of a compound of the         formula (I) and/or a salt thereof, 64 parts by weight of         kaolin-containing quartz as inert substance, 10 parts by weight         of potassium lignosulfonate and 1 part by weight of sodium         oleoylmethyltaurinate as wetting agent and dispersant, and         grinding the mixture in a pinned-disk mill.     -   c) A readily water-dispersible dispersion concentrate is         obtained by mixing 20 parts by weight of a compound of the         formula (I) and/or a salt thereof with 6 parts by weight of         alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight         of isotridecanol polyglycol ether (8 EO) and 71 parts by weight         of paraffinic mineral oil (boiling range for example about 255         to above 277° C.) and grinding the mixture in a ball mill to a         fineness of below 5 microns.     -   d) An emulsifiable concentrate is obtained from 15 parts by         weight of a compound of the formula (I) and/or a salt thereof,         75 parts by weight of cyclohexanone as solvent and 10 parts by         weight of oxethylated nonylphenol as emulsifier.     -   e) Water-dispersible granules are obtained by mixing         -   75 parts by weight of a compound of the formula (I) and/or a             salt thereof,         -   10 parts by weight of calcium lignosulfonate,         -   5 parts by weight of sodium lauryl sulfate,         -   3 parts by weight of polyvinyl alcohol and         -   7 parts by weight of kaolin,         -   grinding the mixture in a pinned-disk mill, and granulating             the powder in a fluidized bed by spraying on water as             granulating liquid.     -   f) Water-dispersible granules are also obtained by homogenizing         and precomminuting, in a colloid mill,         -   25 parts by weight of a compound of the formula (I) and/or a             salt thereof,         -   5 parts by weight of sodium             2,2′-dinaphthylmethane-6,6′-disulfonate,         -   2 parts by weight of sodium oleoylmethyltaurinate,         -   1 part by weight of polyvinyl alcohol,         -   17 parts by weight of calcium carbonate and         -   50 parts by weight of water,         -   subsequently grinding the mixture in a bead mill and             atomizing and drying the resulting suspension in a spray             tower by means of a single-substance nozzle.

A further aspect of present invention is the use of one or more N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to HPPD tolerant plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (III) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) in combination with further HPPD inhibitor herbicide belonging to the class of triketones, such as tembotrione, sulcotrione and mesotrione, or belonging to the class of pyrazolinates, such as pyrasulfotole and topramezone, particularly selected from tembotrione, sulcotrione, topramezone, bicyclopyrone, tefuryltrione and mesotrione, more particularly tembotrione in mixed formulations or in the tank mix, and/or with further known active substances which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by a chemical name, if appropriate together with the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. In this context, one and in some cases also several use forms are mentioned by way of example:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), di-allate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoro-propyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, L-glufosinate, L-glufosinate-ammonium, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, KUH-071, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, methazole, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogen sulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrazolynate (pyrazolate), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, sulf-allate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, TH-547, thenylchlor, thiafluamide, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, tralkoxydim, tri-allate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds

The application rate required of an N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to be applied to areas where HPPD tolerant plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) are growing varies as a function of the external conditions such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha and more of active substance, but it is preferably between 0.005 and 750 g/ha.

In case of combined applications of N-(tetrazol-4-yl)- or N-(triazol-3-yl)arylcarboxamides as defined above or their salts herbicides that differ from N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to the HPPD tolerant plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), these mixtures may cause crop injury, based on the presence herbicides different to N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts. In order to reduce/eliminate such crop injuries, appropriate safeners may be added. These safeners, which are employed in antidotically active amounts, reduce the phytotoxic side effects of herbicides/pesticides used, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), alfalfa, sugar beet, sugarcane, oilseed rape, cotton and soya spp., preferably corn, cotton, sugar beet, or soya spp.

The safeners are preferably selected from the group consisting of:

A) Compounds of the Formula (S-I)

where the symbols and indices have the following meanings:

-   n_(A) is a natural number from 0 to 5, preferably from 0 to 3; -   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or     (C₁-C₄)-haloalkyl; -   W_(A) is an unsubstituted or substituted divalent heterocyclic     radical from the group consisting of partially unsaturated or     aromatic five-membered heterocycles having 1 to 3 hetero ring atoms     of the type N or O, where at least one nitrogen atom and at most one     oxygen atom is present in the ring, preferably a radical from the     group consisting of (W_(A) ¹) to (W_(A) ⁴),

-   m_(A) is 0 or 1; -   R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated or     unsaturated 3- to 7-membered heterocycle having at least one     nitrogen atom and up to 3 heteroatoms, preferably from the group     consisting of O and S, which is attached via the nitrogen atom to     the carbonyl group in (S-I) and which is unsubstituted or     substituted by radicals from the group consisting of (C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy and optionally substituted phenyl, preferably a     radical of the formula OR_(A) ³, NHR_(A) ⁴ or N(CH₃)₂, in particular     of the formula OR_(A) ³; -   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic     hydrocarbon radical having preferably a total of 1 to 18 carbon     atoms; -   R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or     unsubstituted phenyl; -   R_(A) ⁵ is H, (C₁-C₅)-alkyl, (C₁-C₅)-haloalkyl),     (C₁-C₄)-alkoxy-(C₁-C₅)-alkyl, cyano or COOR_(A) ⁹ where R_(A) ⁹ is     hydrogen, (C₁-C₅)-alkyl, (C₁-C₅)-haloalkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,     (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl; -   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are     hydrogen, (C₁-C₅)-alkyl, (C₁-C₅)-haloalkyl, (C₃-C₁₂)-cycloalkyl or     substituted or unsubstituted phenyl;     preferably:     a) compounds of the type of the     dichlorophenylpyrazoline-3-carboxylic acid, preferably compounds     such as ethyl     1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)5-methyl-2-pyrazoline-3-carboxylate     (S1-1) (“mefenpyr-diethyl”, see Pestic. Man.), and related     compounds, as described in WO 91/07874;     b) derivatives of dichlorophenylpyrazolecarboxylic acid, preferably     compounds such as ethyl     1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl     1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3),     ethyl     1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate     (S1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate     (S1-5) and related compounds, as described in EP-A-333 131 and     EP-A-269 806;     c) compounds of the type of the triazolecarboxylic acids, preferably     compounds such as fenchlorazole(-ethyl ester), i.e. ethyl     1-(2,4-dichlorophenyl)-5-trichloro-methyl-(1     H)-1,2,4-triazole-3-carboxylate (S1-6), and related compounds, as     described in EP-A-174 562 and EP-A-346 620;     d) compounds of the type of the 5-benzyl- or     5-phenyl-2-isoxazoline-3-carboxylic acid or the     5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds     such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate     (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and     related compounds, as described in WO 91/08202, or ethyl     5,5-diphenyl-2-isoxazolinecarboxylate (S1-9) (“isoxadifen-ethyl”) or     n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-10) or ethyl     5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as     described in the patent application WO-A-95/07897.

B) Quinoline Derivatives of the Formula (S-II)

where the symbols and indices have the following meanings:

-   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or     (C₁-C₄)-haloalkyl; -   n_(B) is a natural number from 0 to 5, preferably from 0 to 3; -   R_(B) ² OR_(B) ³, SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated     or unsaturated 3- to 7-membered heterocycle having at least one     nitrogen atom and up to 3 heteroatoms, preferably from the group     consisting of O and S, which is attached via the nitrogen atom to     the carbonyl group in (S-II) and is unsubstituted or substituted by     radicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy     or optionally substituted phenyl, preferably a radical of the     formula OR_(B) ³, NHR_(B) ⁴ or N(CH₃)₂, in particular of the formula     OR_(B) ³; -   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic     hydrocarbon radical having preferably a total of 1 to 18 carbon     atoms; -   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or     unsubstituted phenyl; -   T_(B) is a (C₁- or C₂)-alkanediyl chain which is unsubstituted or     substituted by one or two (C₁-C₄)-alkyl radicals or by     [(C₁-C₃)-alkoxy]carbonyl;     preferably:     a) compounds of the type of the 8-quinolinoxyacetic acid (S2),     preferably     1-methylhexyl (5-chloro-8-quinolinoxy)acetate (common name     “cloquintocet-mexyl” (S2-1) (see Pestic. Man.),     1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2),     4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3),     1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate-(S2-4),     ethyl (5-chloro-8-quinolinoxy)acetate (S2-5),     methyl (5-chloro-8-quinolinoxy)acetate (S2-6),     allyl (5-chloro-8-quinolinoxy)acetate (S2-7),     2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate     (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and     related compounds, as described in EP-A-86 750, EP-A-94 349 and     EP-A-191 736 or EP-A-0 492 366, and also their hydrates and salts,     as described in WO-A-2002/034048.     b) Compounds of the type of the (5-chloro-8-quinolinoxy)malonic     acid, preferably compounds such as diethyl     (5-chloro-8-quinolinoxy)malonate, diallyl     (5-chloro-8-quinolinoxy)malonate, methyl ethyl     (5-chloro-8-quinolinoxy)malonate and related compounds, as described     in EP-A-0 582 198.

C) Compounds of the Formula (S-III)

where the symbols and indices have the following meanings:

-   R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,     (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl; -   R_(C) ², R_(C) ³ are identical or different and are hydrogen,     (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,     (C₂-C₄)-haloalkenyl, (C₁-C₄)-alkylcarbamoyl-(C₁-C₄)-alkyl,     (C₂-C₄)-alkenylcarbamoyl-(C₁-C₄)-alkyl,     (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, dioxolanyl-(C₁-C₄)-alkyl, thiazolyl,     furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted     phenyl, or R_(C) ² and R_(C) ³ together form a substituted or     unsubstituted heterocyclic ring, preferably an oxazolidine,     thiazolidine, piperidine, morpholine, hexahydropyrimidine or     benzoxazine ring;     preferably:

Active compounds of the type of the dichloroacetamides which are frequently used as pre-emergence safener (soil-acting safeners), such as, for example,

“dichlormid” (see Pestic. Man.) (=N,N-diallyl-2,2-dichloroacetamide),

“R-29148” (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from Stauffer),

“R-28725” (=3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine from Stauffer),

“benoxacor” (see Pestic. Man.) (=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine),

“PPG-1292” (=N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide from PPG Industries),

“DKA-24” (=N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide from Sagro-Chem),

“AD-67” or “MON 4660” (=3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane from Nitrokemia or Monsanto),

“TI-35” (=1-dichloroacetylazepane from TRI-Chemical RT)

“diclonon” (dicyclonone) or “BAS 145138” or “LAB 145138” (=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane from BASF) and

“furilazole” or “MON 13900” (see Pestic. Man.) (=(RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine).

D) N-Acylsulfonamides of the Formula (S-IV) and their Salts

in which

-   X_(D) is CH or N; -   R_(D) ¹ is CO—NR_(D) ⁵R_(D) ⁶ or NHCO—R_(D) ⁷; -   R_(D) ² is halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, nitro,     (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulfonyl,     (C₁-C₄)-alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl; -   R_(D) ³ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or     (C₂-C₄)-alkynyl; -   R_(D) ⁴ is halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-haloalkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy,     cyano, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,     (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkoxycarbonyl or     (C₁-C₄)-alkylcarbonyl; -   R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,     (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl, phenyl or 3-     to 6-membered heterocyclyl containing v_(D) heteroatoms from the     group consisting of nitrogen, oxygen and sulfur, where the seven     last-mentioned radicals are substituted by v_(D) substituents from     the group consisting of halogen, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,     (C₁-C₂)-alkylsulfinyl, (C₁-C₂)-alkylsulfonyl, (C₃-C₆)-cycloalkyl,     (C₁-C₄)-alkoxycarbonyl, (C₁-C₄)-alkylcarbonyl and phenyl and, in the     case of cyclic radicals, also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl; -   R_(D) ⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or     (C₂-C₆)-alkynyl, where the three last-mentioned radicals are     substituted by v_(D) radicals from the group consisting of halogen,     hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-alkylthio, or -   R_(D) ⁵ and R_(D) ⁶ together with the nitrogen atom carrying them     form a pyrrolidinyl or piperidinyl radical; -   R_(D) ⁷ is hydrogen, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,     (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 last-mentioned     radicals are substituted by v_(D) substituents from the group     consisting of halogen, (C₁-C₄)-alkoxy, halogen-(C₁-C₆)-alkoxy and     (C₁-C₄)-alkylthio and, in the case of cyclic radicals, also     (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl; -   n_(D) is 0, 1 or 2; -   m_(D) is 1 or 2;     v_(D) is 0, 1, 2 or 3;     from among these, preference is given to compounds of the type of     the N-acylsulfonamides, for example of the formula (S-V) below,     which are known, for example, from WO 97/45016

in which

-   R_(D) ⁷ is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2     lat-mentioned radicals are substituted by v_(D) substituents from     the group consisting of halogen, (C₁-C₄)-alkoxy,     halogen-(C₁-C₆)-alkoxy and (C₁-C₄)-alkylthio and, in the case of     cyclic radicals, also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl; -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃; -   m_(D) is 1 or 2; -   v_(D) is 0, 1, 2 or 3;     and also     acylsulfamoylbenzamides, for example of the formula (S-VI) below,     which are known, for example, from WO 99/16744,

for example those in which R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=2-OMe (“cyprosulfamide”, S3-1),

-   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S3-2), -   R_(D) ⁵=ethyl and (R_(D) ⁴)=2-OMe (S3-3), -   R_(D) ⁵=isopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S3-4) and -   R_(D) ⁵=isopropyl and (R_(D) ⁴)=2-OMe (S3-5);     and also     compounds of the type of the N-acylsulfamoylphenylureas of the     formula (S-VII), which are known, for example, from EP-A-365484

in which

-   R_(D) ⁸ and R_(D) ⁹ independently of one another are hydrogen,     (C₁-C₅)-alkyl, (C₃-C₅)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl, -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃ -   m_(D) is 1 or 2;     from among these in particular -   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, -   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, -   1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, -   1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea,     G) active compounds from the class of the hydroxyaromatics and     aromatic-aliphatic carboxylic acid derivatives, for example     ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid,     3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,     4-fluorosalicyclic acid,     1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide,     2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in     WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001;     H) active compounds from the class of the     1,2-dihydroquinoxalin-2-ones, for example     1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,     1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,     1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one     hydrochloride,     1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one,     as described in WO 2005112630,     I) active compounds which, in addition to a herbicidal action     against harmful plants, also have safener action on crop plants such     as rice, such as, for example, “dimepiperate” or “MY-93” (see     Pestic. Man.) (=S-1-methyl-1-phenylethyl     piperidine-1-thiocarboxylate), which is known as safener for rice     against damage by the herbicide molinate,

“daimuron” or “SK 23” (see Pestic. Man.) (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as safener for rice against damage by the herbicide imazosulfuron,

“cumyluron”=“JC-940” (=3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see JP-A-60087254), which is known as safener for rice against damage by a number of herbicides,

“methoxyphenone” or “NK 049” (=3,3′-dimethyl-4-methoxybenzophenone), which is known as safener for rice against damage by a number of herbicides,

“CSB” (=1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No. 54091-06-4 from Kumiai), which is known as safener against damage by a number of herbicides in rice,

K) compounds of the formula (S-IX),

-   -   as described in WO-A-1998/38856

in which the symbols and indices have the following meanings:

-   R_(K) ¹, R_(K) ² independently of one another are halogen,     (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,     (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, nitro; -   A_(K) is COOR_(K) ³ or COOR_(K) ⁴ -   R_(K) ³, R_(K) ⁴ independently of one another are hydrogen,     (C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl,     (C₁-C₄)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,     pyridinylalkyl or alkylammonium, -   n_(K) ¹ is 0 or 1, -   n_(K) ², n_(K) ³ independently of one another are 0, 1 or 2     preferably: methyl (diphenylmethoxy)acetate (CAS Reg. No.:     41858-19-9),     L) compounds of the formula (S-X),     -   as described in WO A-98/27049

in which the symbols and indices have the following meanings:

-   X_(L) is CH or N, -   n_(L) is, in the case that X=N, an integer from 0 to 4 and,     -   in the case that X=CH, an integer from 0 to 5, -   R_(L) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,     (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,     (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkoxycarbonyl, optionally     substituted phenyl, optionally substituted phenoxy, -   R_(L) ² is hydrogen or (C₁-C₄)-alkyl, -   R_(L) ³ is hydrogen, (C₁-C₅)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl     or aryl, where each of the carbon-containing radicals mentioned     above is unsubstituted or substituted by one or more, preferably by     up to three, identical or different radicals from the group     consisting of halogen and alkoxy; or salts thereof,     M) active compounds from the class of the     3-(5-tetrazolylcarbonyl)-2-quinolones, for example -   1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone     (CAS Reg. No.: 219479-18-2),     1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone     (CAS Reg. No.: 95855-00-8), as described in WO-A-1999000020,     N) compounds of the formula (S-XI) or (S-XII),     -   as described in WO-A-2007023719 and WO-A-2007023764

in which

-   R_(N) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃, OCF₃ -   Y, Z independently of one another are O or S, -   n_(N) is an integer from 0 to 4, -   R_(N) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,     aryl, benzyl, halobenzyl, -   R_(N) ³ is hydrogen, (C₁-C₆)alkyl,     O) one or more compounds from the group consisting of: -   1,8-naphthalic anhydride, -   O,O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfoton), -   4-chlorophenyl methylcarbamate (mephenate), -   O,O-diethyl O-phenyl phosphorothioate (dietholate), -   4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS     Reg. No.: 31541-57-8), -   2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838, CAS     Reg. No.: 133993-74-5), -   methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate     (from WO-A-98/13361; CAS Reg. No.: 205121-04-6), -   cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), -   1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), -   4′-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime     (fluxofenim), -   4,6-dichloro-2-phenylpyrimidine (fenclorim), -   benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate     (flurazole), -   2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),

including the stereoisomers, and the salts customary in agriculture.

A mixture of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above or their salts to be applied in connection with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil structure improvers to transgenic plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (III) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37), is likewise possible.

Some of the safeners are already known as herbicides and accordingly, in addition to the herbicidal action against harmful plants, also act by protecting the crop plants. The weight ratios of herbicide (mixture) to safener generally depend on the herbicide application rate and the effectiveness of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably from 100:1 to 1:100, in particular from 20:1 to 1:20. The safeners may be formulated analogously to the compounds of the formula (I) or their mixtures with other herbicides/pesticides and be provided and used as a finished formulation or as a tank mix with the herbicides.

The required application rate of the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides as defined above to areas where such transgenic plants containing one or more chimeric gene(s) (I) comprising a DNA sequence encoding hydroxyphenylpyruvate dioxygenase (HPPD) (I) derived from a member of a group of organisms, consisting of (a) Avena, preferably Avena sativa, more preferably comprising a DNA sequence identical to SEQ ID No. 1 encoding HPPD defined by SEQ ID No. 2, (b) Pseudomonas, preferably Pseudomonas fluorescens, more preferably comprising a DNA sequence identical to SEQ ID No. 3 encoding HPPD defined by SEQ ID No. 4, (c) Synechococcoideae, preferably Synechococcus sp., more preferably comprising a DNA sequence identical to SEQ ID No. 6, encoding HPPD defined by SEQ ID No. 7, (d) Blepharismidae, preferably Blepharisma japonicum, more preferably comprising a DNA sequence identical to SEQ ID No. 8 encoding HPPD defined by SEQ ID No. 9, (e) Rhodococcus, preferably Rhodococcus sp. (strain RHA1), isolate ro03041 more preferably comprising a DNA sequence identical to SEQ ID No. 10 encoding HPPD defined by SEQ ID No. 11, or Rhodococcus sp. (strain RHA1), isolate ro02040, more preferably comprising a DNA sequence identical to SEQ ID No. 12 encoding HPPD defined by SEQ ID No. 13, (f) Picrophilaceae, preferably Picrophilus torridus, more preferably comprising a DNA sequence identical to SEQ ID No. 14 encoding HPPD defined by SEQ ID No. 15, (g) Kordia, preferably Kordia algicida, more preferably comprising a DNA sequence identical to SEQ ID No. 16 encoding HPPD defined by SEQ ID No. 17, or (II) comprising one or more mutated DNA sequences of HPPD encoding genes of the before defined organisms, preferably mutants as described in WO 2010/085705, U.S. Pat. No. 6,245,968, WO 2009/144079, WO2011/076877, WO2011/076882, WO2011/076892, WO2011/076885, WO2011/076889, WO 2012/021785, according to the latter, comprising more especially one or more mutated DNA sequences of HPPD encoding genes obtained from maize (Zea mays) or soybean (Glycine max), especially preferable HPPD encoding genes from maize (Zea mays) or (Ill) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), (ii) comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gin) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or (IV) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas (=Comamonas) testosteroni HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->S (Ser) replacement at position 352, and an A (Ala)->E (Glu) replacement at position 356 (named Axmi428H-Evo40 and being disclosed under SEQ ID No 55 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 32), (ii) comprising a E (Glu)->P (Pro) replacement at position 351, a G (Gly)->W (Trp) replacement at position 352, a K (Lys)->A (Ala) replacement at position 355 and an A (Ala)->Q (Gln) replacement at position 356 (named Axmi428H-Evo41 and being disclosed under SEQ ID No 56 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 33), or (V) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas aeruginosa strain ATX22717 HPPD protein comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->S (Ser) replacement at position 338, and an A (Ala)->E (Glu) replacement at position 342 (named Axmi305H-Evo40 and being disclosed under SEQ ID No 51 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 40), (ii) comprising a E (Glu)->P (Pro) replacement at position 337, a G (Gly)->W (Trp) replacement at position 338, a K (Lys)->A (Ala) replacement at position 341 and an A (Ala)->Q (Gln) replacement at position 342 (named Axmi305H-Evo41 and being disclosed under SEQ ID No 52 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 41), or (VI) comprising a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas agarici HPPD protein (i) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named Axmi309H-Evo40 and being disclosed under SEQ ID No 53 in PCT/US2013/59598, and being disclosed in present application as the HPPD protein sequence under SEQ ID No 36), (ii) comprising a E (Glu)->P (Pro) replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named Axmi309H-EVO41 and being disclosed under SEQ ID No 54 in PCT/US2013/59598 and being disclosed in present application as the HPPD protein sequence under SEQ ID No 37) varies depending, inter alia, on external conditions such as temperature, humidity and the type of herbicide used. It can vary within wide limits, for example between 0.001 and 10 000 g/ha or more of active substance; however, it is preferably between 0.5 and 5000 g/ha, particularly preferably between 0.5 and 1000 g/ha and very particularly preferably between 0.5 and 500 g/ha.

SEQUENCES LISTING

-   SEQ ID No. 1: Nucleic acid sequence encoding Avena sativa HPPD     optimized for the expression in E. coli cells -   SEQ ID No. 2: Protein encoded by SEQ ID No. 1 -   SEQ ID No. 3: Nucleic acid sequence encoding Pseudomonas fluorescens     HPPD mutated at position 336; mutation Gly=>Trp (Pfw336) -   SEQ ID No. 4: Protein encoded by SEQ ID No. 3 (PfHPPD336W) -   SEQ ID No. 5: Nucleic acid sequence encoding Pseudomonas fluorescens     HPPD mutated at position 336; mutation Gly=>Trp; optimized for the     expression in soybean and cotton -   SEQ ID No. 6: Nucleic acid sequence encoding Synechococcus sp. HPPD -   SEQ ID No. 7: Protein encoded by SEQ ID No. 6 -   SEQ ID No. 8: Nucleic acid sequence encoding Blepharisma japonicum     HPPD (FMP37) -   SEQ ID No. 9: Protein encoded by SEQ ID No. 8 -   SEQ ID No. 10: Nucleic acid sequence encoding Rhodococcus sp.     (strain RHA1), isolate ro03041 HPPD (FMP22) -   SEQ ID No. 11: Protein encoded by SEQ ID No. 10 -   SEQ ID No. 12: Nucleic acid sequence encoding Rhodococcus sp.     (strain RHA1), isolate ro02040 HPPD -   SEQ ID No. 13: Protein encoded by SEQ ID No. 12 -   SEQ ID No. 14: Nucleic acid sequence encoding Picrophilus torridus     HPPD -   SEQ ID No. 15: Protein encoded by SEQ ID No. 14 -   SEQ ID No. 16: Nucleic acid sequence encoding Kordia algicida HPPD     (FMP27) -   SEQ ID No. 17: Protein encoded by SEQ ID No. 16 -   SEQ ID No. 18: Nucleic acid sequence encoding Synechococcus sp. HPPD     optimized for the expression in soybean and cotton -   SEQ ID No. 19: Nucleic acid sequence encoding Blepharisma japonicum     HPPD optimized for the expression in soybean and cotton -   SEQ ID No. 20: Nucleic acid sequence encoding Rhodococcus sp.     (strain RHA1), isolate ro0341 HPPD optimized for the expression in     soybean and cotton -   SEQ ID No. 21: Nucleic acid sequence encoding Rhodococcus sp.     (strain RHA1), isolate ro0240 HPPD optimized for the expression in     soybean and cotton -   SEQ ID No. 22: Nucleic acid sequence encoding Picrophilus torridus     HPPD optimized for the expression in soybean and cotton -   SEQ ID No. 23: Nucleic acid sequence encoding Kordia algicida HPPD     optimized for the expression in soybean and cotton -   SEQ ID No 24 Nucleic acid sequence encoding Pseudomonas fluorescens     HPPD (PfH PPD-Evo33)     -   mutated at position 335, mutation Glu=>Pro;     -   and mutated at position 336; mutation Gly=>Trp -   SEQ ID No 25 Protein encoded by SEQ ID No 24. -   SEQ ID No 26 Nucleic sequence encoding Pseudomonas fluorescens HPPD     (PfHPPD-Evo40) mutated at position 335, mutation Glu-->Pro,     -   mutated at position 336, mutation Gly-->Ser,     -   and mutated at position 340, mutation Ala-->Glu -   SEQ ID No 27 Protein encoded by SEQ ID No 26. -   SEQ ID No 28 Nucleic acid sequence encoding Pseudomonas fluorescens     HPPD (PfHPPD-Evo41)     -   mutated at position 335, mutation Glu-->Pro,     -   mutated at position 336, mutation Gly-->Trp,     -   mutated at position 339, mutation Lys-->Ala,     -   and mutated at position 340, mutation Ala-->Gln -   SEQ ID No 29 Protein encoded by SEQ ID No 28. -   SEQ ID No 30 Nucleic acid sequence encoding Pseudomonas (=Comamonas)     testosterone Axmi428H HPPD -   SEQ ID No 31 Protein encoded by SEQ ID No 30. -   SEQ ID No 32 Protein sequence of Pseudomonas (=Comamonas)     testosteroni Axmi428H HPPD (Axmi428-Evo40)     -   Mutated at position 351, mutation Glu-->Pro,     -   mutated at position 352, mutation Gly-->Ser, and     -   mutated at position 356, mutation Ala-->Glu -   SEQ ID No 33 Protein sequence of Pseudomonas (=Comamonas)     testosteroni Axmi428H HPPD (Axmi428-Evo41)     -   mutated at position 351, mutation Glu-->Pro,     -   mutated at position 352, mutation Gly-->Trp,     -   mutated at position 355, mutation Lys-->Ala, and     -   mutated at position 356, mutation Ala-->Gln -   SEQ ID No 34 Nucleic acid sequence encoding Pseudomonas agarici     Axmi309H HPPD. -   SEQ ID No 35 Protein encoded by SEQ ID No 34. -   SEQ ID No 36 Protein sequence of Pseudomonas agarici Axmi309H HPPD     (Axmi309-Evo40)     -   mutated at position 335, mutation Glu-->Pro,     -   mutated at position 336, mutation Gly-->Ser, and     -   mutated at position 340, mutation Ala-->Glu -   SEQ ID No 37 Protein sequence of Pseudomonas agarici Axmi309H HPPD     (Axmi309-Evo41)     -   mutated at position 335, mutation Glu-->Pro,     -   mutated at position 336, mutation Gly-->Trp,     -   mutated at position 339, mutation Lys-->Ala, and     -   mutated at position 340, mutation Ala-->Gln -   SEQ ID No 38 Nucleic acid encoding of Pseudomonas aeruginosa     Axmi305H HPPD. -   SEQ ID No 39 Protein encoded by SEQ ID No 38. -   SEQ ID No 40 Protein sequence of Pseudomonas aeruginosa Axmi305H     (Axmi305-Evo40)     -   mutated at position 337, mutation Glu-->Pro,     -   mutated at position 338, mutation Gly-->Ser, and     -   mutated at position 342, mutation Ala-->Glu -   SEQ ID No 41 Protein sequence of Pseudomonas aeruginosa Axmi305H     (Axmi305-Evo41)     -   mutated at position 337, mutation Glu-->Pro,     -   mutated at position 338, mutation Gly-->Trp,     -   mutated at position 341, mutation Lys-->Ala, and     -   mutated at position 342, mutation Ala-->Gln -   SEQ ID NO 42 HPPD protein encoded by Avena sativa SEQ ID No 43 HPPD     protein as of SEQ ID No 42 having a deletion at position 109 (Avena     sativa Δ A109). -   SEQ ID No 44 HPPD protein encoded by Zea mays. -   SEQ ID No 45 Nucleic acid encoding of Pseudomonas fluorescens HPPD     (PfHPPD). -   SEQ ID No 46 Protein encoded by SEQ ID No 45.

EXAMPLES

A. Cloning of Avena HPPD (According WO02/46387)

A1—Cloning for Expression in E. coli Cells

cDNA coding for Avena sativa HPPD (AvHPPD; SEQ ID No. 1) was ordered at GeneArt (Regensburg, Germany) using the codon usage optimized for the expression of the gene in Escherichia coli cells. Upstream to the start codon ATG, was added the sequence corresponding to the recognition site of the restriction enzyme BamHI, and downstream to the stop codon was added the sequence stretch corresponding to the recognition site of the enzyme HindIII. The synthesized fragment was cloned using the restriction enzymes BamHI and HindIII in the previously opened vector pET32a (Novagen, Darmstadt, Germany), in order to obtain a fusion with the HisTag present in the vector at the N-Terminal extremity from the AvHPPD protein (SEQ ID No. 2). The resulting vector was named pET32a-AvHPPDe.

The protein was produced in E. coli and isolated following the standard protocol (as described for example in WO2009/144079).

B Cloning of PfHPPD-G336W

B1—Cloning of PfHPPD-G336W for the Expression in E. coli Cells

The gene coding for the mutant HPPD G336W (SEQ ID No. 3) (U.S. Pat. No. 6,245,968) from Pseudomonas fluorescens in the plasmid pKK233-2 (Clontech) (U.S. Pat. No. 6,245,968) was used as template for a PCR to add to the sequence at it 5′ extremity the sequence corresponding to the recognition site of the enzyme NcoI and at its 3′ extremity the sequence corresponding to the recognition site of the enzyme XbaI. (see WO 2009/144079). The cloning was made in order to obtain a His tag fusion protein at the N-terminal extremity of the Pseudomonas HPPD G336W, also called PfW336 or PfG336W or PfHPPDW336 (SEQ ID No. 4) named “pSE420(RI)NX-PfG336W”.

B2—Cloning of PfHPPD-G336W for the Expression in Plants

A binary vector for tobacco or soybean transformation is, for example, constructed with the CaMV35 promoter driving the expression of the gene PfHPPD-G336W (SEQID No 5), with a codon usage optimized for the expression in dicotyledoneous plants and at its 5′ extremity was added a sequence coding for an OTP, and further upstream a sequence TEV (Tobacco etch virus) to improve the stability of the mRNA in plants followed by the CaMV35S terminator. Additionally, the transformation vector also contains a PAT gene cassette in which the gene is driven by a CaVM35S promoter and followed by a CaMV35S terminator for glufosinate based selection during the transformation process and a 2 mEPSPS gene cassette in which the gene is driven by an histone promoter from Arabidopsis to confer tolerance to the herbicide glyphosate to the transformed plants. The binary vector was called pFCO117.

All other mutated Pseudomonas genes and genes obtained from other organisms according to this invention can be cloned in analogy to the above.

B3—Alternative Approach for Cloning of HPPD Genes into a Plant Expression Cassette.

For each of the HPPD genes described herein, the open reading frame (ORF) is amplified by PCR from a full-length DNA template. Hind III restriction sites are added to each end of the ORFs during PCR. Additionally, the nucleotide sequence ACC is added immediately 5′ to the start codon of the gene to increase translational efficiency (Kozak (1987) Nucleic Acids Research 15:8125-8148; Joshi (1987) Nucleic Acids Research 15:6643-6653). The PCR product is cloned and sequenced using techniques well known in the art to ensure that no mutations are introduced during PCR.

The plasmid containing the PCR product is digested with Hind III and the fragment containing the intact ORF is isolated. This fragment is cloned into the Hind III site of a plasmid such as pAX200, a plant expression vector containing the rice actin promoter (McElroy et al. (1991) Molec. Gen. Genet. 231:150-160) and the PinII terminator (An et al. (1989) The Plant Cell 1:115-122). The promoter—gene—terminator fragment from this intermediate plasmid is then sub cloned into plasmid pSB11 (Japan Tobacco, Inc.) to form a final pSB11-based plasmid. These pSB11-based plasmids are typically organized such that the DNA fragment containing the promoter—gene—terminator construct may be excised by double digestion by restriction enzymes, such as Kpn I and Pme I, and used for transformation into plants by aerosol beam injection. The structure of the resulting pSB11-based clones is verified by restriction digest and gel electrophoresis, and by sequencing across the various cloning junctions.

The plasmid is mobilized into Agrobacterium tumefaciens strain LBA4404 which also harbors the plasmid pSB1 (Japan Tobacco, Inc.), using triparental mating procedures well known in the art, and plating on media containing spectinomycin. The pSB11-based plasmid clone carries spectinomycin resistance but is a narrow host range plasmid and cannot replicate in Agrobacterium. Spectinomycin resistant colonies arise when pSB11-based plasmids integrate into the broad host range plasmid pSB1 through homologous recombination. The cointegrate product of pSB1 and the pSB11-based plasmid is verified by Southern hybridization. The Agrobacterium strain harboring the cointegrate is used to transform maize by methods known in the art, such as, for example, the PureIntro method (Japan Tobacco).

C Mutation of the Various HPPD Enzymes

C1—Generation Point Mutants (as Described in Detail in PCT/US2013/59598)

The Pfw336 mutant was further mutagenized at several positions. Randomization of these positions was carried out using the QUIKCHANGE® lightning kit. The theoretical diversity of the library was about 300. Mutants were pooled and transformed into DH5α E. coli cells. Six hundred individual clones were screened for tolerance to the HPPD inhibitor tembotrione (TBT). The clones were grown in LB media plus kanamycin at 37 degrees C. in a shaker until an OD600 nm of 0.3 was reached. Cultures were then switched to 30 degrees C. and incubated for an additional 17 hours. Cultures were spun down and cell pellets resuspended in 10 mM Hepes/KOH pH 7.6, 4 mM MgCl2, 1 mM DTT. The cells were lysed by bead beating and soluble cell extracts were obtained after centrifugation. The mutants were analyzed using a brown color assay. Specifically, the HPPD extracts were assayed in 96 well format for HPPD inhibitor tolerance by spotting on solid media containing LB-agar, kanamycin, 5 mM tyrosine, 42 mM succinate and an HPPD inhibitor. In the primary screen, 20 ul extract was spotted in triplicate on plates containing 250 uM tembotrione. Plates were covered with airpore tape and incubated at 37 degrees C. After 24 hours, brown pigment formation was visually compared to a sample containing PfHPPD336W. Variants showing increased pigment formation in the presence of TBT were re-assayed on 250 uM TBT and 250 uM diketonitrile (DKN) active compound of isoxaflutole (IFT). Those variants that again showed improved inhibitor tolerance were again expressed, and extract was titrated on 250 uM TBT and 250 uM DKN to determine the extent of improvement. Extract samples were also analyzed by SDS-PAGE and the extracts were found to contain equal amounts of HPPD protein.

C2—Generation of Permutational Library (as Described in Detail in PCT/US2013/59598)

The sequences of the top performing first-generation variants were analyzed and a permutational library in the region combining positions 335, 336, 339, 340 was generated. Screening was carried out as described under C1, above. Titration data below shows variant PfHPPDEvo40 had improved tolerance to TBT and DKN compared to PfHPPD336W. SDS-PAGE analysis was carried out and showed no differences in HPPD expression levels between variants.

Variants were also tested by plating whole E. coli cells expressing HPPDs on media containing various HPPD inhibitors. For these experiments, DH5α cells containing HPPD expressing plasmids were grown in LB media+kanamycin until an OD600 nm=0.5 was reached. Serial dilutions of cells were prepared in LB media+kanamycin corresponding to OD600 values of 0.016, 0.008, 0.004, and 0.002. Ten microliters of each dilution were plated in triplicate on plates containing no HPPD inhibitor, 250 uM TBT, 250 uM DKN and 250 uM mesotrione (MST). Plates were incubated for 18 hours at 37 degrees C. SDS-PAGE analysis was carried out and showed no differences in HPPD expression levels between variants.

C3—Preparation of Pseudomonas fluorescens HPPD Mutant G336W (Pfw336) and Kinetic Characterization of the HPPD Enzymes.

The native Pseudomonas fluorescens HPPD nucleotide sequence (PfHPPD, 1077 bp, as described in WO2009144079), which encodes the amino acid sequence listed herein as SEQ ID No 45, and as described in WO2009144079, WO 96/38567, and in Rüetschi et al. (Eur. J. Biochem., 205, 459-466, 1992), was initially cloned into the unique NcoI site of the expression vector pKK233-2 (Pharmacia) that provides a start codon.

At the 5′ end, directly downstream to the ATG, a nucleic acid sequence encoding an alanine amino acid and a nucleic acid sequence encoding an N-terminal HIS6-Tag was inserted. Upstream to the ATG, two additional cytosine base pairs were added in order to obtain a sequence corresponding to the recognition site of the restriction enzyme NcoI and downstream to the stop codon the sequences corresponding to the recognition site of the restriction enzyme XbaI were added. The DNA sequence corresponding to the gene, including the sequence encoding the HIS-TAG, was cut with the restriction enzymes NcoI and XbaI, and then cloned into the modified expression vector pSE420(RI)NX (5261 bp). The cloning and expression vector pSE420(RI)NX (5261 bp) is based on the plasmid pSE420 by Invitrogen (Karlsruhe, Germany). Modifications of this vector include the addition of a nptII gene (neomycin phosphotransferase; Sambrook and Russell, 2001, Molecular Cloning: a laboratory manual (Third edition)) conferring tolerance to the antibiotic kanamycin and which is missing the majority of the superlinker region (multiple cloning site).

The plasmid possesses the trp-lac (trc) promoter and the lacl^(q) gene that provides the lac repressor in every E. coli host strain. The lac repressor binds to the lac operator (lacO) and restricts expression of the target gene; this inhibition can be alleviated by induction with Isopropyl β-D-1-thiogalactopyranoside (IPTG).

The resulting vector was called pSE420(RI)NX-PfHPPD and it was used to transform Escherichia coli BL21 cells (Merck, Darmstadt, Germany).

Expression of HPPD was carried out in E. coli K-12 BL21 containing pSE420(RI)NX-PfHPPD or pSE420(RI)NX-Pfw336 (for details, see under B1, above). Cells were allowed to grow until OD reached 0.5, then expression was initiated from the trp-lac (trc) promoter by induction with 1 mM IPTG which binds to the lac repressor and causes its dissociation from the lac operon. Expression was carried out over 15 h at 28° C.

To prepare the pre-starter culture, 2 mL of TB medium (100 μg*mL⁻¹ carbenicillin) were inoculated with 50 μL of an E. coli K-12 BL21 glycerol stock. The pre-starter culture was incubated at 37° C. with shaking at 140 rpm for 15 h. 200 μl of the pre-starter culture was used to initiate the starter culture (5 mL TB supplement with 100 μg*L⁻¹), which was incubated 3 h at 37° C.

To prepare the main culture, 400 mL of TB medium (100 μg*mL⁻¹ carbenicillin) were inoculated with 4 mL of the starter culture. This starter culture was incubated at 37° C. with shaking at 140 rpm until OD₆₀₀ 0.5 was reached. Then recombinant protein expression was induced with 400 μl of 1M IPTG solution. The cells were allowed to grow for an additional hour under these conditions, then the temperature was lowered to 28° C. and the culture was shaken at 140 rpm for 15 h. Cells were harvested by centrifugation at 6000×g for 15 min at 4° C. Then cell pellets were stored at −80° C.

D—Production of HPPD Protein in E. coli, Purification Via His-Tag

All above defined E. coli expression vectors were used to transform Escherichia coli BL21 cells (Merck, Darmstadt, Germany).

Expression of HPPD was carried out in E. coli K-12 BL21 containing pQE30-AtHPPD, pET32a-AvHPPDe, pSE420(RI)NX-Pfw336, pSE420(RI)NX-FMP27 (see WO2011/076889 or pSE420(RI)NX-FMP37 (see WO2011/076882). Cells were allowed to grow until OD reached 0.5, then expression was initiated from the trp-lac (trc) promoter by induction with 1 mM IPTG which binds to the lac repressor and causes its dissociation from the lac operon. Expression was carried out over 15 h at 28° C.

To prepare the pre-starter culture, 2 mL of TB medium (100 μg*mL⁻¹ carbenicillin) were inoculated with 50 μL of an E. coli K-12 BL21 glycerol stock. The pre-starter culture was incubated at 37° C. with shaking at 140 rpm for 15 h. 200 μl of the pre-starter culture was used to initiate the starter culture (5 mL TB supplement with 100 μg*L⁻¹), which was incubated 3 h at 37° C.

To prepare the main culture, 400 mL of TB medium (100 μg*mL⁻¹ carbenicillin) were inoculated with 4 mL of the starter culture. This starter culture was incubated at 37° C. with shaking at 140 rpm until OD₆₀₀ 0.5 was reached. Then recombinant protein expression was induced with 400 μl of 1M IPTG solution. The cells were allowed to grow for an additional hour under these conditions, then the temperature was lowered to 28° C. and the culture was shaken at 140 rpm for 15 h. Cells were harvested by centrifugation at 6000×g for 15 min at 4° C. Then cell pellets were stored at −80° C.

D1—Isolation and Purification of his₆-Tagged HPPD in Native Form Lysis of Cells

Cells were lysed using Lysozyme, an enzyme that cleaves the 1,4-β-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan which forms the bacterial cell wall. Cell membranes were then disrupted by the internal pressure of the bacterial cell. In addition, the lysis buffer contained Benzonase® Nuclease, an endonuclease that hydrolyzes all forms of DNA and RNA without damaging proteins and thereby largely reduces viscosity of the cell lysate. Lysis under native conditions was carried out on ice.

For purification of His₆-tagged proteins the QIAexpress® Ni-NTA Fast Start Kit was used following the user manual instruction.

D2—Purification of his₆-Tagged Proteins by Immobilized Metal Ion Affinity Chromatography (IMAC)

The cleared cell lysate (10 mL) obtained after centrifugation of the lysis reaction was loaded onto a Ni-NTA Fast Start Column from the QIAexpress® Ni-NTA Fast Start Kit (Qiagen, Hilden, Germany) and purification was carried out according to the instruction manual. The His₆-tagged protein was eluted with 2.5 mL of elution buffer.

D3—Desalting of HPPD Solutions by Gel Filtration

HPPD solutions eluted from a Ni-NTA Fast Start Column with 2.5 mL of elution buffer were applied to a Sephadex G-25 PD-10 column (GE Healthcare, Freiburg, Germany) following the user manual instruction. After the whole sample had entered the gel bed, elution was performed with 3.5 mL of storage buffer.

The HPPD solutions eluted from the desalting column were frozen at −80° C. in 1 mL aliquots.

D4—Determination of HPPD Protein Concentration Using the Bradford Protein Assay

Protein concentration was determined using the standard Bradford assay (Bradford, (1976), Anal Biochem 72: 248-254).

D5—Determination of Purity of HPPD Solutions Using SDS-PAGE

The integrity of the eluted protein was checked by SDS-PAGE protein gel electrophoresis using the gel NuPAGE® Novex 4-12% Bis-Tris Gels (Invitrogen, Karlsruhe, Germany), approximately 10 μg of protein were loaded. 10 μL of Laemmli Sample Buffer was added to 1-10 μL of protein solution and the mixture was incubated at 90° C. for 10 min. After short centrifugation step, the whole mixture was loaded into a slot of an SDS gel previously fixed in a XCell SureLock™ Novex Mini-Cell gel chamber filled with NuPAGE® MOPS SDS Running Buffer (diluted from the 20×-solution with ddH₂O). A voltage of 150 was then applied to the gel chamber for 1 h. For staining of protein bands, the gel was immersed in Coomassie Brilliant Blue R-250 Staining Solution. For destaining of the polyacrylamide gel, it was immersed in Coomassie Brilliant Blue R-250 Destaining Solution until protein bands appear blue on a white gel.

E—Determination of HPPD Activity in Presence of N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides

HPPD activity was measured at room temperature by adding appropriate amounts of HPPD to a solution of 200 mM Tris-HCl pH 7.6, 10 mM ascorbate, 20 μM FeSO₄, 650 units of catalase, 8 μg HGA dioxygenase (HGA: homogentisate) and 600 μM HPP in a total volume of 1 ml. Initial reaction rates in the absence or presence of inhibitors were determined from the increase in absorbance at 318 nm due to the formation of maleylacetoacetate (ϵ318=11,900 M−1 cm−1). pI50-values (the negative log values of the concentration of inhibitor necessary to inhibit 50% of the enzyme activity in molar concentration were determined from dose-response plots of HPPD activity versus inhibitor concentrations tested (0.1 to 100 μM) using the 4 Parameter Logistic Model or Sigmoidal Dose-Response Model of the ID Business Solutions Ltd. XLfit software suite. Due to the UV absorption of the HPPD inhibitors tested, inhibitor concentrations >100 μM could not be tested. In cases, the symbol “>” is used this means that the value was far higher than the one indicated but could not be precisely calculated within in the range of concentration of inhibitor tested.

All results are shown in Table 8.

In the 1^(st) column of Table 8, the chemical compound employed in the assay is named (according to the numbering of the Tables 1 to 7, above). In columns 2, 3, 4, and 5 the pI50-values of the corresponding chemical compounds against various HPPD enzymes (name and SEQ ID Nos are indicated, respectively) are given.

TABLE 8 Avena PfHPPD PfHPPD HPPD FMP 37 Evo 40 Evo 41 SEQ ID SEQ ID SEQ ID SEQ ID Compound No 2 No 9 No 27 No 29 5-145 5.5 5.0 >5.3 >5.3 2-145 5.8 5.0 5.3 5.3 6-37 4.4 3.8 3.9 3.8 7-132 4.8 5.1 3.7 3.6 2-360 5.4 4.7 4.8 4.7 2-361 5.8 4.9 5.3 5.1 2-363 5.8 5.0 5.2 4.9 2-144 5.4 4.9 5.2 5.0 2-364 5.8 5.1 4.9 4.5

These data show that the HPPD derived from various organisms do show an acceptable tolerance levels to several N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides.

F—Soybean Transformation and Herbicide Tolerance Evaluation of Transgenic Plants Expressing Mutated DNA Sequences of HPPD Encoding Genes

F1—Soybean Transformation and T0 Plant Establishment

Soybean transformation was achieved by using methods by best mode well known in the art, such as the one described using the Agrobacterium tumefaciens mediated transformation soybean half-seed explants using essentially the method described by Paz et al. (2006), Plant cell Rep. 25:206. Transformants were identified using various HPPD inhibitors tembotrione or isoxaflutole as selection marker. The appearance of green shoots can be observed, and documented as an indicator of tolerance to the respective herbicide. The tolerant transgenic shoots showed normal greening comparable to wild-type soybean shoots not treated with the respective HPPD inhibitor, whereas wild-type soybean shoots treated with the same amount of the respective HPPD inhibitor was entirely bleached. This indicates that the presence of the HPPD protein enables the tolerance to HPPD inhibitor herbicides.

Tolerant green shoots are transferred to rooting media or grafted. Rooted plantlets are transferred to the greenhouse after an acclimation period. Plants containing the transgene are then sprayed with HPPD inhibitor herbicides, as for example with tembotrione at a rate of 100 to 200 g Al/ha supplemented with ammonium sulfate and methyl ester raps oil or with mesotrione at a rate of 100 to 400 g Al/ha supplemented with ammonium sulfate and methyl ester raps oil. Ten days after the application the symptoms due to the application of the herbicide are evaluated and compared to the symptoms observed on a wild type plants under the same conditions. Tolerant T0 soybean plants obtained according to the above were advanced to the T1 generation.

F2—Greenhouse Trials with Transgenic Soybean T2 Plants

In this herbicide efficacy testing the established T2 plants harbor an expression vector, which contained at least one chimeric gene encoding a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), or comprising an E (Glu)->P (Pro) replacement at position 335, a G (Gly)->S (Ser) replacement at position 336, and an A (Ala)->E (Glu) replacement at position 340 (named PfHPPDEvo40 and being disclosed under SEQ ID No:8 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 27), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or expressing the variant of the Pseudomonas fluorescens HPPD protein PfHPPD-G336W described in patent WO99/24585,

T2 events were germinated and grown in the greenhouse and sprayed at the V2-V3 stage of soybean development with one exemplary N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide of formulation type WP20 (concentration range of 6.25 g Al/ha-75 g Al/ha) supplemented with ammonium sulfate and methylated rape seed oil (Actirob).

As a spray control, wild type soybean (Merlin and Thorne) and the above mentioned transgenic T2 soybean plants have been sprayed with the spray mixture lacking the herbicide. Herbicide tolerance of all plants in the experiment was evaluated fourteen days after treatment (DAT). Plants were rated visually with the following herbicide tolerance classes: “0”=marginal tolerance; 41%-100% damaged leaf area; “1”=moderate tolerance; 26%-40% damaged leaf area; “2”=good tolerance; 16%-25% damaged leaf area; “3”=high tolerance; less than or equal to 15% damaged leaf area.

TABLE 9 Evaluation of the HPPD inhibitor tolerance from T2 soybean transgenic events expressing the variant of the Pseudomonas fluorescens HPPD protein PfHPPD-G336W (WO99/24585), or PfHPPD-Evo33, or PfHPPD-Evo40, or PfHPPD-Evo41 (PCT/US2013/59598) versus wild type (wt) soybean plants (Merlin and Thorne). Plants were treated with one exemplary N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide (Compound “2-145”; Table 2) with a final concentration of 6.25, 25, 50, or 75 g Al/ha. Herbicide tolerance has been scored after 14 days of treatment. As a control, wild type soybean and transgenic soybean T2 plants were treated with a spray mix lacking the herbicide. All these control plants did not show bleached leaf area. Following leaf area damage classes have been defined for herbicide tolerance scoring: “0” = marginal tolerance; 41%-100% damaged leaf area; “1” = moderate tolerance; 26%-40% damaged leaf area; “2” = good tolerance; 16%-25% damaged leaf area; “3” = high tolerance; 0% - less than or equal to 15% damaged leaf area. Herbicide tolerance scoring Soybean “0” “1” “2” “3” Total number Events Number of plants tested and categorized events Treatment: Compound “2-145” with 6.25 g Al/ha Merlin (wt) 4 0 0 0 4 Thorne (wt) 4 0 0 0 4 PfHPPD-Evo33 0 0 0 12 12 PfHPPD-Evo40 0 0 0 8 8 PfHPPD-Evo41 0 1 0 11 12 PfHPPD-W336 1 0 0 11 12 Treatment: Compound “2-145” with 25 g Al/ha Merlin 4 0 0 0 4 Thorne 4 0 0 0 4 PfHPPD-Evo33 1 1 0 14 16 PfHPPD-Evo40 0 0 0 12 12 PfHPPD-Evo41 0 0 0 16 16 PfHPPD-W336 0 2 3 11 16 Treatment: Compound “2-145” with 50 g Al/ha PfHPPD-Evo33 0 0 1 3 4 PfHPPD-Evo40 0 0 0 4 4 PfHPPD-Evo41 0 0 2 2 4 PfHPPD-W336 0 0 1 3 4 Treatment: Compound “2-145” with 75 g Al/ha PfHPPD-Evo33 0 0 0 4 4 PfHPPD-Evo40 0 0 0 4 4 PfHPPD-Evo41 0 0 0 4 4 PfHPPD-W336 0 1 0 3 4

The transgenic T2 soybean plants expressing the mutated DNA sequences of HPPD encoding genes had a superior tolerance compared to the controls with several events tolerant to agronomic relevant levels of the exemplary N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide.

G—Cotton Transformation, Selection and Herbicide Tolerance Evaluation of Transgenic Plants Expressing Mutated DNA Sequences of HPPD Encoding Genes

G1—Cotton Transformation and T0 Plant Establishment

Cotton transformation is achieved by using methods well known in the art, especially preferred method in the one described in the PCT patent publication WO 00/71733. Regenerated plants were transferred to the greenhouse. Following an acclimation period, sufficiently grown plants were sprayed with HPPD inhibitor herbicides as for example tembotrione equivalent to 100 gAl/ha or with mesotrione equivalent to 100 to 200 g Al/ha supplemented with ammonium sulfate and methyl ester raps oil. Seven days after the spray application, the symptoms due to the treatment with the herbicide were evaluated and compared to the symptoms observed on wild type cotton plants subjected to the same treatment under the same conditions. Obtained tolerant T0 plants were selected and advanced for T1 generation.

G2—Field Studies of HPPD Inhibitor Tolerant T3 Transgenic Cotton Plants

To further test the performance of generated HPPD tolerant cotton plants under field conditions a study was conducted at two locations.

In particular, several independent events harbor a cotton optimized plant expression cassette, which contained and expressed at least one chimeric gene encoding a mutated DNA sequence described in PCT/US2013/59598, more specifically a mutated sequence of the Pseudomonas fluorescens HPPD protein (i) comprising an E (Glu)->P (Pro) replacement at position 335 and a G (Gly)->W (Trp) replacement at position 336 (named PfHPPDEvo33 and being disclosed under SEQ ID No:6 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 25), or (iii) comprising an E (Glu)->P (Pro)replacement at position 335, a G (Gly)->W (Trp) replacement at position 336, a K (Lys)->A (Ala) replacement at position 339 and an A (Ala)->Q (Gln) replacement at position 340 (named PfHPPDEvo41 and being disclosed under SEQ ID No:16 in PCT/US2013/59598 and being disclosed in present application under SEQ ID No. 29), or expressing the variant of the Pseudomonas fluorescens HPPD protein PfHPPD-G336W describe in patent WO99/24585, were analyzed.

The studies were designed as follows and well known to those skilled in the art: The plots were kept free of weed with a pre-planting treatment of a non-selective herbicide. Control rows were set-up with the non-transgenic cotton variety “Cocker” and the respective transgenic cotton events, which have been treated with a spray mix lacking the different herbicides. Cotton plants were treated with herbicides at V3 stage. Up to three replications have been set-up and conducted and the average maximum phytotoxicity has been summarized in Table 10, below.

Post-emergence application has been conducted with the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide compound “2-145” with a final concentration of 200 g Al/ha and scored after 14 days (Table 10).

The control treatments did not show bleached leaf area. The variety “Cocker” showed at least 87% and up to 98% leaf damage. The following leaf area damage (phytotoxicity) classes have been defined based on visually herbicide tolerance scoring:

-   -   “0”=marginal/agronomic non-relevant tolerance; greater than 20%         damaged leaf area;     -   “1”=moderate tolerance/agronomic non-relevant tolerance; 16%-20%         damaged leaf area;     -   “2”=good tolerance; greater than 10% and up to 15% damaged leaf         area;     -   “3”=high tolerance; less than or equal to 10% damaged leaf area.

TABLE 10 Evaluation of the HPPD inhibitor tolerance from T3 cotton transgenic events expressing the variant of the Pseudomonas fluorescens HPPD protein PfHPPD-G336W (WO99/24585), or PfHPPD-Evo33, or PfHPPD-Evo41 (PCT/US2013/59598). The control variety “Cocker” showed under all treatment conditions at least 87% leaf damage with up to 98%. Results are shown for plants treated with N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide compound “2-145” (Table 2) with a final concentration of 200 g Al/ha. Plants have been treated after emergence in developmental stage V3 (post-emergence) and scored after 14 days As a control non-transgenic and transgenic cotton plants were always treated with a spray mix lacking the herbicide. All these control plants did not show bleached leaf area. Following leaf area damage (phytotoxicity) classes have been defined for herbicide tolerance scoring: “0” = marginal tolerance; >20% damaged leaf area; “1” = moderate tolerance; 16%-20% damaged leaf area; “2” = good tolerance; 11%-15% damaged leaf area; “3” = high tolerance; 0%-10% damaged leaf area. Independent cotton events Average maximum phytotoxicity harboring the variant of scoring with Compound “2-145” the PfHPPD protein [200 g Al/ha] PfHPPD-Evo33 Evo33/1 3 Evo33/2 3 Evo33/3 3 Evo33/4 3 Evo33/5 3 Evo33/6 3 PfHPPD-Evo41 Evo41/1 3 Evo41/2 3 Evo41/3 3 Evo41/4 3 Evo41/5 3 Evo41/6 3 Evo41/7 3 Evo41/8 3 Evo41/9 3 Evo41/10 3 Evo41/11 3 Evo41/12 2 Evo41/13 3 Evo41/14 3 Evo41/15 3 PfHPPD-W336 W336/1 2 W336/2 2 W336/3 2

Most of the transgenic cotton plants expressing a variant of HPPD encoding genes had an agronomic relevant tolerance level against N-(1,3,4-Oxadiazol-2-yl)arylcarboxamides. These field studies showed for the first time that it is possible to generate crop plants tolerant to N-(1,3,4-Oxadiazol-2-yl) arylcarboxamides by over-expressing mutated HPPD encoding genes in the crop of interest.

H—Transformation of Maize Plant Cells by Agrobacterium-Mediated Transformation

Ears are best collected 8-12 days after pollination. Embryos were isolated from the ears, and those embryos 0.8-1.5 mm in size were preferred for use in transformation. Embryos were plated scutellum side-up on a suitable incubation media, and incubated overnight at 25° C. in the dark.

However, it is not necessary per se to incubate the embryos overnight. Embryos were contacted with an Agrobacterium strain containing the appropriate vectors having a nucleotide sequence of the present invention for Ti plasmid mediated transfer for about 5-10 min, and then plated onto co-cultivation media for about 3 days (25° C. in the dark). After co-cultivation, explants were transferred to recovery period media for about five days (at 25° C. in the dark). Explants were incubated in selection media for up to eight weeks, depending on the nature and characteristics of the particular selection utilized. After the selection period, the resulting callus were transferred to embryo maturation media, until the formation of mature somatic embryos were observed. The resulting mature somatic embryos were then placed under low light, and the process of regeneration was initiated the best mode as known in the art. The resulting shoots are allowed to root on rooting media, and the resulting plants are transferred to nursery pots and propagated as transgenic plants.

All publications and patent applications mentioned in the specification are indicative of the level of skill of those skilled in the art to which this invention pertains. All publications and patent applications are herein incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference.

Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be obvious that certain changes and modifications may be practiced within the scope of the appended claims. 

The invention claimed is:
 1. A method for controlling unwanted plants comprising applying an N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide of formula (I) or a salt thereof

wherein X is methyl, Y is SO₂CH₃, and Z is CF₃, to a transgenic crop plant that is tolerant to an HPPD inhibitor herbicide by containing one or more chimeric gene(s), wherein the one or more chimeric gene(s) comprises a DNA sequence derived from Pseudomonas fluorescens encoding a hydroxyphenylpyruvate dioxygenase (HPPD) selected from the group consisting of SEQ ID NO: 25, SEQ ID NO: 27, and SEQ ID NO:
 29. 2. The method according to claim 1, wherein the transgenic crop plant belongs to the group of dicotyledonous crops consisting of Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, and Vicia, or to the group of monocotyledonous crops consisting of Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea.
 3. The method according to claim 1 wherein the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide or salt thereof is applied in combination with one or more HPPD inhibitor herbicides selected from triketone or pyrazolinate herbicide in mixed formulations or in a tank mix; and/or with one or more-inhibitors of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase; and/or with a growth regulator.
 4. The method according to claim 3, wherein the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide or salt thereof is applied in combination with one or more HPPD inhibitor herbicides selected from the group consisting of tembotrione, mesotrione, bicyclopyrone, tefuryltrione pyrasulfotole, pyrazolate, diketonitrile, topramezone, benzofenap, and sulcotrione.
 5. The method according to claim 2, wherein the transgenic crop plant is a Glycine plant.
 6. The method according to claim 1, wherein at least one chimeric gene contained in the transgenic crop comprises a DNA encoding a HPPD consisting of SEQ ID NO:29.
 7. The method according to claim 4, wherein the one or more HPPD inhibitor herbicides is mesotrione.
 8. The method for controlling unwanted plants according to claim 1 wherein the application of the N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide of formula (I) and/or salt thereof is to (a) the unwanted plants, (b) to the seeds of unwanted plants, and/or (c) to the area on which the plants grow.
 9. The method according to claim 1, wherein at least one chimeric gene contained in the transgenic crop comprises a DNA encoding a HPPD consisting of SEQ ID NO:25.
 10. The method according to claim 1, wherein at least one chimeric gene contained in the transgenic crop comprises a DNA encoding a HPPD consisting of SEQ ID NO:27.
 11. The method according to claim 2, wherein the transgenic crop plant is a Gossypium plant. 